Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts

Journal of the American Chemical Society

Volumn 122, Issue 34, 2000, Pages 8168-8179

  Garber, Steven B ^a   Kingsbury, Jason S ^a   Gray, Brian L ^a   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ETHER DERIVATIVE; LIGAND; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; GEL CHROMATOGRAPHY; SYNTHESIS;

EID: 0034734340     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001179g     Document Type: Article

References (115)

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17. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
18. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
19. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
20. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
21. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
22. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
23. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
24. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
25. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
26. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
27. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
28. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
29. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
30. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
31. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
32. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
33. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
34. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035-3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
35. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
36. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
37. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D.
38. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655-1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
39. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
40. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
41. For the use of metal-containing dendrimers in homogeneous catalysis, see: (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482-5490. (b) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659-663. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285. (d) Brunner, H.; Furst, J. Tetrahedron, 1994, 50, 4303. (e) Brunner, H.; Bublak, P. Synthesis 1995, 36. (f) Brunner, H.; Net, G. Synthesis, 1995, 423. (g) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46. (h) Bolm, C.; Derrien, N.; Seger, A. Synlett, 1996, 387-388. (i) Seebach, D., Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710-1740. (j) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027-2032. (k) Sellner, H.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1918-1920. (l) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236. (m) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526-1529. (n) Reetz, M. T. Top. Catal. 1997, 4, 187-200. (o) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274-10275. (p) Schneider, R.; Kollner, C.; Weber, I.; Togni, A. J. Chem. Soc., Chem. Commun. 1999, 2415-2416. (q) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783-3786. (r) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528-7536. (s) Bourque, S. C.; Maltais, F.; Xiao, W.-J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121, 3035- 3038. (t) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122, 956-957. (u) Oosterom, G. E.; van Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1119-1120. (v) de Groot, D.; Eggeling, E. B.; de Wilde, J. C.; Kooijman, H.; van Haaren, R. J.; van der Made, A. W.; Spek, A. L.; Vogt, D.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1999, 1623-1624. (w) Hovestad, N. J.; Eggeling, E. B.; Heidbuchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1655- 1658. (x) Kleij, A. W.; Gossage, R. A.; Jastrzebski, J. T. B. H.; Boersma, J.; van Koten, G. Angew. Chem., Int. Ed. Engl. 2000, 39, 176-178. (y) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. J. Chem. Soc., Chem. Commun. 2000, 789-790. (z) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621-1624.
42. For recent general reviews on dendrimers, see: (a) Peerlings, H. W. I.; Meijer, E. W. Chem.-Eur. J. 1997, 3, 1563-1570. (b) Smith, D. K.; Diederich, F. Chem.-Eur. J. 1998, 4, 1353-1361. (c) Majoral, J.-P.; Caminade, A.-M. Chem. Rev. 1999, 99, 845-880. For a review of organometallic and related metal-containing dendrimers, see: (d) Newkome, G. R.; Moorefield, C. N.; Vogtle, F.; Dendritic Molecules: Concepts, Syntheses, Perspectives; VCH: Weinheim, 1998; pp 210-222. (e) Hearshaw, M. A.; Moss, J. R. J. Chem. Soc., Chem. Commun. 1998, 1-8. (f) Newkome, G. R.; He, E.; Moorefield, C. N. Chem. Rev. 1999, 99, 1689- 1746.
43. For recent general reviews on dendrimers, see: (a) Peerlings, H. W. I.; Meijer, E. W. Chem.-Eur. J. 1997, 3, 1563-1570. (b) Smith, D. K.; Diederich, F. Chem.-Eur. J. 1998, 4, 1353-1361. (c) Majoral, J.-P.; Caminade, A.-M. Chem. Rev. 1999, 99, 845-880. For a review of organometallic and related metal-containing dendrimers, see: (d) Newkome, G. R.; Moorefield, C. N.; Vogtle, F.; Dendritic Molecules: Concepts, Syntheses, Perspectives; VCH: Weinheim, 1998; pp 210-222. (e) Hearshaw, M. A.; Moss, J. R. J. Chem. Soc., Chem. Commun. 1998, 1-8. (f) Newkome, G. R.; He, E.; Moorefield, C. N. Chem. Rev. 1999, 99, 1689- 1746.
44. For recent general reviews on dendrimers, see: (a) Peerlings, H. W. I.; Meijer, E. W. Chem.-Eur. J. 1997, 3, 1563-1570. (b) Smith, D. K.; Diederich, F. Chem.-Eur. J. 1998, 4, 1353-1361. (c) Majoral, J.-P.; Caminade, A.-M. Chem. Rev. 1999, 99, 845-880. For a review of organometallic and related metal-containing dendrimers, see: (d) Newkome, G. R.; Moorefield, C. N.; Vogtle, F.; Dendritic Molecules: Concepts, Syntheses, Perspectives; VCH: Weinheim, 1998; pp 210-222. (e) Hearshaw, M. A.; Moss, J. R. J. Chem. Soc., Chem. Commun. 1998, 1-8. (f) Newkome, G. R.; He, E.; Moorefield, C. N. Chem. Rev. 1999, 99, 1689- 1746.
45. For recent general reviews on dendrimers, see: (a) Peerlings, H. W. I.; Meijer, E. W. Chem.-Eur. J. 1997, 3, 1563-1570. (b) Smith, D. K.; Diederich, F. Chem.-Eur. J. 1998, 4, 1353-1361. (c) Majoral, J.-P.; Caminade, A.-M. Chem. Rev. 1999, 99, 845-880. For a review of organometallic and related metal-containing dendrimers, see: (d) Newkome, G. R.; Moorefield, C. N.; Vogtle, F.; Dendritic Molecules: Concepts, Syntheses, Perspectives; VCH: Weinheim, 1998; pp 210-222. (e) Hearshaw, M. A.; Moss, J. R. J. Chem. Soc., Chem. Commun. 1998, 1-8. (f) Newkome, G. R.; He, E.; Moorefield, C. N. Chem. Rev. 1999, 99, 1689- 1746.
46. For recent general reviews on dendrimers, see: (a) Peerlings, H. W. I.; Meijer, E. W. Chem.-Eur. J. 1997, 3, 1563-1570. (b) Smith, D. K.; Diederich, F. Chem.-Eur. J. 1998, 4, 1353-1361. (c) Majoral, J.-P.; Caminade, A.-M. Chem. Rev. 1999, 99, 845-880. For a review of organometallic and related metal-containing dendrimers, see: (d) Newkome, G. R.; Moorefield, C. N.; Vogtle, F.; Dendritic Molecules: Concepts, Syntheses, Perspectives; VCH: Weinheim, 1998; pp 210-222. (e) Hearshaw, M. A.; Moss, J. R. J. Chem. Soc., Chem. Commun. 1998, 1-8. (f) Newkome, G. R.; He, E.; Moorefield, C. N. Chem. Rev. 1999, 99, 1689- 1746.
47. For recent general reviews on dendrimers, see: (a) Peerlings, H. W. I.; Meijer, E. W. Chem.-Eur. J. 1997, 3, 1563-1570. (b) Smith, D. K.; Diederich, F. Chem.-Eur. J. 1998, 4, 1353-1361. (c) Majoral, J.-P.; Caminade, A.-M. Chem. Rev. 1999, 99, 845-880. For a review of organometallic and related metal-containing dendrimers, see: (d) Newkome, G. R.; Moorefield, C. N.; Vogtle, F.; Dendritic Molecules: Concepts, Syntheses, Perspectives; VCH: Weinheim, 1998; pp 210-222. (e) Hearshaw, M. A.; Moss, J. R. J. Chem. Soc., Chem. Commun. 1998, 1-8. (f) Newkome, G. R.; He, E.; Moorefield, C. N. Chem. Rev. 1999, 99, 1689-1746.
48. For general discussions on advantages and disadvantages of dendrimers over solid-phase systems, see: (a) Tomalia, D. A.; Dvornic, P. R. Nature 1994, 372, 617-618. (b) Haggin, J. Chem. Eng. News 1995, 73, 26-27.
49. For general discussions on advantages and disadvantages of dendrimers over solid-phase systems, see: (a) Tomalia, D. A.; Dvornic, P. R. Nature 1994, 372, 617-618. (b) Haggin, J. Chem. Eng. News 1995, 73, 26-27.
50. For other reports on recyclable Ru-based metathesis catalysts (in addition to ref 1a), see: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195-200. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657- 8662. (c) Barrett, A. G. M.; Cramp, S. M.; Roberts, R. S. Org. Lett. 1999, 1, 1083-1086.
51. For other reports on recyclable Ru-based metathesis catalysts (in addition to ref 1a), see: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195-200. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657-8662. (c) Barrett, A. G. M.; Cramp, S. M.; Roberts, R. S. Org. Lett. 1999, 1, 1083-1086.
52. For other reports on recyclable Ru-based metathesis catalysts (in addition to ref 1a), see: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195-200. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657- 8662. (c) Barrett, A. G. M.; Cramp, S. M.; Roberts, R. S. Org. Lett. 1999, 1, 1083-1086.
53. (a) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
54. (b) Chatterjee, A. K.; Grubbs, R. G. Org. Lett. 1999, 1, 1751-1753.
55. (c) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784.
56. (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 2490-2493.
57. (b) Weskamp, T.; Kohl, F. J.; Hieringer, W.; Gleich, D.; Herrmann, W. A. Angew. Chem., Int. Ed. Engl. 1999, 38, 2416-2419.
58. (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247-2250.
59. (d) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
60. (e) Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F. J.; Herrmann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790.
61. (f) Furstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207.
62. For comprehensive reviews of nucleophilic carbenes, see: (a) Regitz, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 725-728. (b) Herrmann, W. A.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187. (c) Arduengo, A. J., III.; Krafczyk, R. Chem.-Ztg. 1998, 32, 6-14. (d) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913-921.
63. For comprehensive reviews of nucleophilic carbenes, see: (a) Regitz, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 725-728. (b) Herrmann, W. A.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187. (c) Arduengo, A. J., III.; Krafczyk, R. Chem.-Ztg. 1998, 32, 6-14. (d) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913-921.
64. For comprehensive reviews of nucleophilic carbenes, see: (a) Regitz, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 725-728. (b) Herrmann, W. A.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187. (c) Arduengo, A. J., III.; Krafczyk, R. Chem.-Ztg. 1998, 32, 6-14. (d) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913-921.
65. For comprehensive reviews of nucleophilic carbenes, see: (a) Regitz, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 725-728. (b) Herrmann, W. A.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187. (c) Arduengo, A. J., III.; Krafczyk, R. Chem.-Ztg. 1998, 32, 6-14. (d) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913-921.
66. The route shown below was also examined but proved to be less efficient (32% isolated yield is unoptimized; MES = 2,4,6-trimethylphenyl). See the Experimental Section for details of the synthesis of the imidazolinium salt.
67. 3 for Z = 4; T = 293(2) K. The crystal lattice contained methylene chloride. Further details, including tables of crystallographic data, are available in the Supporting Information.
68. Ru complex 3 is equally efficient in effecting the RCM reactions in Table 2. For example, catalytic RCM of 7, 11, and 13 proceeds in the presence of 5 mol % 3 and in a similar length of time as that for 5 (22 °C) to afford the desired products 8, 12, and 14 in 93%, 64%, and 72% yield, respectively. It is worth noting that all previously reported reactions promoted by 3 were carried out at 45 °C (see ref 8).
69. For a recent report on the accelerating effect of an α-hydroxyl group on Ru-catalyzed RCM reactions, see Hoye, T. R.; Zhao, H. Org. Lett. 1999, 1, 1123-1125.
70. 3). For other studies on Ru catalyst decomposition and longevity, see: (a) Ulman, M.; Grubbs, R. H. J. Org. Chem. 1999, 64, 7202-7207. (b) Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375-5380.
71. 3). For other studies on Ru catalyst decomposition and longevity, see: (a) Ulman, M.; Grubbs, R. H. J. Org. Chem. 1999, 64, 7202-7207. (b) Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375-5380.
72. 2 returns to its original styrene ligand faster than reacting with a substrate-disubstituted olefin (i.e., initiation is not the problem). For the application of diallyl ether or ethylene to metal-catalyzed metathesis, see: (a) Reference 1b. (b) Reference 1c. (c) Johannes, C. W.; Visser, M. S.; Weatherhead G. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 8340-8347. (d) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082-6083. (e) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 129-131. (f) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829.
73. 2 returns to its original styrene ligand faster than reacting with a substrate-disubstituted olefin (i.e., initiation is not the problem). For the application of diallyl ether or ethylene to metal- catalyzed metathesis, see: (a) Reference 1b. (b) Reference 1c. (c) Johannes, C. W.; Visser, M. S.; Weatherhead G. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 8340-8347. (d) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082-6083. (e) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 129-131. (f) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829.
74. 2 returns to its original styrene ligand faster than reacting with a substrate-disubstituted olefin (i.e., initiation is not the problem). For the application of diallyl ether or ethylene to metal- catalyzed metathesis, see: (a) Reference 1b. (b) Reference 1c. (c) Johannes, C. W.; Visser, M. S.; Weatherhead G. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 8340-8347. (d) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082-6083. (e) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 129-131. (f) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829.
75. 2 returns to its original styrene ligand faster than reacting with a substrate-disubstituted olefin (i.e., initiation is not the problem). For the application of diallyl ether or ethylene to metal- catalyzed metathesis, see: (a) Reference 1b. (b) Reference 1c. (c) Johannes, C. W.; Visser, M. S.; Weatherhead G. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 8340-8347. (d) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082-6083. (e) Lautens, M.; Hughes, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 129-131. (f) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829.
76. For studies on Ru-catalyzed ROM/RCM processes, see: (a) ref 16a-b. (b) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640. (c) Burke, S. D.; Quinn, K. J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626-8627.
77. For studies on Ru-catalyzed ROM/RCM processes, see: (a) ref 16a- b. (b) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640. (c) Burke, S. D.; Quinn, K. J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626-8627.
78. For studies on Ru-catalyzed ROM/CM processes, see: (a) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610-9611. (b) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. (c) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257-259. (d) Cuny, G. D.; Cao, J.; Hauske, J. R. Tetrahedron Lett. 1997, 38, 5237-5240. (e) Cao, J.; Cuny, G. D.; Hauske, J. R. Mol. Diversity 1998, 3, 173-179.
79. For studies on Ru-catalyzed ROM/CM processes, see: (a) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610- 9611. (b) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. (c) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257-259. (d) Cuny, G. D.; Cao, J.; Hauske, J. R. Tetrahedron Lett. 1997, 38, 5237-5240. (e) Cao, J.; Cuny, G. D.; Hauske, J. R. Mol. Diversity 1998, 3, 173-179.
80. For studies on Ru-catalyzed ROM/CM processes, see: (a) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610- 9611. (b) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. (c) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257-259. (d) Cuny, G. D.; Cao, J.; Hauske, J. R. Tetrahedron Lett. 1997, 38, 5237-5240. (e) Cao, J.; Cuny, G. D.; Hauske, J. R. Mol. Diversity 1998, 3, 173-179.
81. For studies on Ru-catalyzed ROM/CM processes, see: (a) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610- 9611. (b) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. (c) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257-259. (d) Cuny, G. D.; Cao, J.; Hauske, J. R. Tetrahedron Lett. 1997, 38, 5237-5240. (e) Cao, J.; Cuny, G. D.; Hauske, J. R. Mol. Diversity 1998, 3, 173-179.
82. For studies on Ru-catalyzed ROM/CM processes, see: (a) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610- 9611. (b) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479. (c) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257-259. (d) Cuny, G. D.; Cao, J.; Hauske, J. R. Tetrahedron Lett. 1997, 38, 5237-5240. (e) Cao, J.; Cuny, G. D.; Hauske, J. R. Mol. Diversity 1998, 3, 173-179.
83. (a) McKean, D. R.; Parrinello, G.; Renaldo, A. F.; Stille, J. K. J. Org. Chem. 1987, 52, 422-424.
84. For a related review, see: (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1998, 50, 1-652.
85. For carbosilane dendimer structures based on a repetitive alkenylation/hydrosilation sequence, see: (a) van der Made, A. W.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1992, 1400-1401. (b) van der Made, A. W.; van Leeuwen, P. W. N. M.; de Wilde, J. C.; Brandes, R. A. C. Adv. Mater. 1993, 5, 466-468. (c) Roovers, J.; Toporowski, P. M.; Zhou, L.-L. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 182. (d) Zhou, L.-L.; Roovers, J. Macromolecules 1993, 26, 963. (e) Roovers, J.; Zhou, L.-L.; Toporowski, P. M.; van der Zwan, M.; Iatrou, H.; Hadjichristidis, N. Macromolecules 1993, 26, 4324. (f) Seyferth, D.; Son, D. Y.; Rheingold, A. L.; Ostrander, R. L. Organometallics 1994, 13, 2682-2690.
86. For carbosilane dendimer structures based on a repetitive alkenylation/hydrosilation sequence, see: (a) van der Made, A. W.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1992, 1400-1401. (b) van der Made, A. W.; van Leeuwen, P. W. N. M.; de Wilde, J. C.; Brandes, R. A. C. Adv. Mater. 1993, 5, 466-468. (c) Roovers, J.; Toporowski, P. M.; Zhou, L.-L. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 182. (d) Zhou, L.-L.; Roovers, J. Macromolecules 1993, 26, 963. (e) Roovers, J.; Zhou, L.-L.; Toporowski, P. M.; van der Zwan, M.; Iatrou, H.; Hadjichristidis, N. Macromolecules 1993, 26, 4324. (f) Seyferth, D.; Son, D. Y.; Rheingold, A. L.; Ostrander, R. L. Organometallics 1994, 13, 2682-2690.
87. For carbosilane dendimer structures based on a repetitive alkenylation/hydrosilation sequence, see: (a) van der Made, A. W.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1992, 1400-1401. (b) van der Made, A. W.; van Leeuwen, P. W. N. M.; de Wilde, J. C.; Brandes, R. A. C. Adv. Mater. 1993, 5, 466-468. (c) Roovers, J.; Toporowski, P. M.; Zhou, L.-L. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 182. (d) Zhou, L.-L.; Roovers, J. Macromolecules 1993, 26, 963. (e) Roovers, J.; Zhou, L.-L.; Toporowski, P. M.; van der Zwan, M.; Iatrou, H.; Hadjichristidis, N. Macromolecules 1993, 26, 4324. (f) Seyferth, D.; Son, D. Y.; Rheingold, A. L.; Ostrander, R. L. Organometallics 1994, 13, 2682-2690.
88. For carbosilane dendimer structures based on a repetitive alkenylation/hydrosilation sequence, see: (a) van der Made, A. W.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1992, 1400-1401. (b) van der Made, A. W.; van Leeuwen, P. W. N. M.; de Wilde, J. C.; Brandes, R. A. C. Adv. Mater. 1993, 5, 466-468. (c) Roovers, J.; Toporowski, P. M.; Zhou, L.-L. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 182. (d) Zhou, L.-L.; Roovers, J. Macromolecules 1993, 26, 963. (e) Roovers, J.; Zhou, L.-L.; Toporowski, P. M.; van der Zwan, M.; Iatrou, H.; Hadjichristidis, N. Macromolecules 1993, 26, 4324. (f) Seyferth, D.; Son, D. Y.; Rheingold, A. L.; Ostrander, R. L. Organometallics 1994, 13, 2682-2690.
89. For carbosilane dendimer structures based on a repetitive alkenylation/hydrosilation sequence, see: (a) van der Made, A. W.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1992, 1400-1401. (b) van der Made, A. W.; van Leeuwen, P. W. N. M.; de Wilde, J. C.; Brandes, R. A. C. Adv. Mater. 1993, 5, 466-468. (c) Roovers, J.; Toporowski, P. M.; Zhou, L.-L. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 182. (d) Zhou, L.-L.; Roovers, J. Macromolecules 1993, 26, 963. (e) Roovers, J.; Zhou, L.-L.; Toporowski, P. M.; van der Zwan, M.; Iatrou, H.; Hadjichristidis, N. Macromolecules 1993, 26, 4324. (f) Seyferth, D.; Son, D. Y.; Rheingold, A. L.; Ostrander, R. L. Organometallics 1994, 13, 2682-2690.
90. For carbosilane dendimer structures based on a repetitive alkenylation/hydrosilation sequence, see: (a) van der Made, A. W.; van Leeuwen, P. W. N. M. J. Chem. Soc., Chem. Commun. 1992, 1400-1401. (b) van der Made, A. W.; van Leeuwen, P. W. N. M.; de Wilde, J. C.; Brandes, R. A. C. Adv. Mater. 1993, 5, 466-468. (c) Roovers, J.; Toporowski, P. M.; Zhou, L.-L. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 182. (d) Zhou, L.-L.; Roovers, J. Macromolecules 1993, 26, 963. (e) Roovers, J.; Zhou, L.-L.; Toporowski, P. M.; van der Zwan, M.; Iatrou, H.; Hadjichristidis, N. Macromolecules 1993, 26, 4324. (f) Seyferth, D.; Son, D. Y.; Rheingold, A. L.; Ostrander, R. L. Organometallics 1994, 13, 2682-2690.
91. For carbosilane dendimers based on a repetitive alkenylation/ hydroboration/oxidation sequence, see: Kim, C.; Son, S.; Kim, B. J. Organomet. Chem. 1999, 588, 1-8.
92. 3 followed by alkylation of the 12 Si-Cl bonds with allylmagnesium bromide should lead to a 12-branch dendritic core structure. Synthesis and study of these and related dendrimers are in progress.
93. 13C NMR spectroscopy, elemental analysis, and mass spectrometry. See the Experimental Section for details.
94. 13% loss of Ru constitutes a 7% loss of the total mass of the fully metalated dendrimer. The reported quantitative (>98%) mass balance for the purified macromolecule is based on a theoretical yield which has been corrected for the minor loss of the metal and its associated ligands.
95. (a) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887-3897. (b) Reference 1a.
96. For a report on a related monophosphine and catalytically active Ru complex, see: (c) Tallarico, J. A.; Bonitatebus, P. J.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157-7158.
97. 3 ligand. The unusual stability of 1 is a result of steric congestion at the transition metal center (the corresponding methyl ether complex is significantly less stable) and thermodynamic stability provided by a styrene ether ligand.
98. The relative inability of 4 to remove Ru from the dendritic structure, in contrast to 34, is noteworthy and may be due to steric factors; electronic issues may also play a role in this reactivity difference, where electronically mismatched systems undergo cross metathesis more effectively. See: Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58-71 and references therein.
99. Analysis of the unpurified reaction mixture indicates that approximately 3% of the Ru loss (3% loss of the total Ru sites) may be due to the isolation of the cross-metathesis product ii, which is presumably formed upon release of the transition metal from the dendrimer (33). The formation of compounds such as ii only occurs with substrates that do not contain terminal alkenes. Otherwise, as shown in Scheme 2, the terminal styrenyl alkoxide is formed upon Ru departure. Presumably, most of ii is reverted back to dendritic 33 through reaction with the Ru-methylene complex. Ru return may occur via ii through formation of the 1,1-disubstituted Ru-carbene followed by intramolecular RCM. Alternatively, cross-metathesis at the conjugated alkene can either afford 33 and the diene precursor to 22 or give the terminal styrene olefin and the Ru-carbene precursor to 22. Regardless, all of the above possibilities eventually afford 22 and recover 33. The recovery of 3% ii may be due to competitive Ru-methylene decomposition.
100. It is not clear whether diene 36 is formed in the reaction of monomeric catalyst 5 (see Scheme 2); analysis of the outcome of the reaction promoted by monomeric 5 was complicated by the presence of the inseparable Ru complex (5).
101. Although the recovered dendrimer is relatively less loaded with lower catalyst loading (78% return for 0.25 mol % 33 versus 90-95% for 1.25 mol % 33), the amount of recovered Ru per mmole of product formed is nearly identical for both conditions.
102. For Mo-catalyzed asymmetric RCM reactions, see: (a) Alexander, J. B.; La, D. S.; Cefalo, D. R.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 4041-4042. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720-9721. (c) Zhu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251-8259. (d) Fujimura, O.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2499-2500. (e) Fujimura, O.; Grubbs, R. H. J. Org. Chem. 1998, 63, 824-832. For application of catalytic asymmetric RCM in target- oriented synthesis see: (f) Burke, S. D.; Muller, N.; Beudry, C. M. Org. Lett. 1999, 1, 1827-1829. For Mo-catalyzed asymmetric ROM reactions see: (g) La, D. S.; Ford, J. G.; Sattely, E. S.; Bonitatebus, P. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 11603-11604. (h) Reference 16f.
103. For Mo-catalyzed asymmetric RCM reactions, see: (a) Alexander, J. B.; La, D. S.; Cefalo, D. R.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 4041-4042. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720-9721. (c) Zhu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251-8259. (d) Fujimura, O.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2499-2500. (e) Fujimura, O.; Grubbs, R. H. J. Org. Chem. 1998, 63, 824-832. For application of catalytic asymmetric RCM in target- oriented synthesis see: (f) Burke, S. D.; Muller, N.; Beudry, C. M. Org. Lett. 1999, 1, 1827-1829. For Mo-catalyzed asymmetric ROM reactions see: (g) La, D. S.; Ford, J. G.; Sattely, E. S.; Bonitatebus, P. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 11603-11604. (h) Reference 16f.
104. For Mo-catalyzed asymmetric RCM reactions, see: (a) Alexander, J. B.; La, D. S.; Cefalo, D. R.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 4041-4042. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720-9721. (c) Zhu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251-8259. (d) Fujimura, O.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2499-2500. (e) Fujimura, O.; Grubbs, R. H. J. Org. Chem. 1998, 63, 824-832. For application of catalytic asymmetric RCM in target- oriented synthesis see: (f) Burke, S. D.; Muller, N.; Beudry, C. M. Org. Lett. 1999, 1, 1827-1829. For Mo-catalyzed asymmetric ROM reactions see: (g) La, D. S.; Ford, J. G.; Sattely, E. S.; Bonitatebus, P. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 11603-11604. (h) Reference 16f.
105. For Mo-catalyzed asymmetric RCM reactions, see: (a) Alexander, J. B.; La, D. S.; Cefalo, D. R.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 4041-4042. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720-9721. (c) Zhu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251-8259. (d) Fujimura, O.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2499-2500. (e) Fujimura, O.; Grubbs, R. H. J. Org. Chem. 1998, 63, 824-832. For application of catalytic asymmetric RCM in target- oriented synthesis see: (f) Burke, S. D.; Muller, N.; Beudry, C. M. Org. Lett. 1999, 1, 1827-1829. For Mo-catalyzed asymmetric ROM reactions see: (g) La, D. S.; Ford, J. G.; Sattely, E. S.; Bonitatebus, P. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 11603-11604. (h) Reference 16f.
106. For Mo-catalyzed asymmetric RCM reactions, see: (a) Alexander, J. B.; La, D. S.; Cefalo, D. R.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 4041-4042. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720-9721. (c) Zhu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251-8259. (d) Fujimura, O.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2499-2500. (e) Fujimura, O.; Grubbs, R. H. J. Org. Chem. 1998, 63, 824-832. For application of catalytic asymmetric RCM in target- oriented synthesis see: (f) Burke, S. D.; Muller, N.; Beudry, C. M. Org. Lett. 1999, 1, 1827-1829. For Mo-catalyzed asymmetric ROM reactions see: (g) La, D. S.; Ford, J. G.; Sattely, E. S.; Bonitatebus, P. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 11603-11604. (h) Reference 16f.
107. For Mo-catalyzed asymmetric RCM reactions, see: (a) Alexander, J. B.; La, D. S.; Cefalo, D. R.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 4041-4042. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720-9721. (c) Zhu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251-8259. (d) Fujimura, O.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2499-2500. (e) Fujimura, O.; Grubbs, R. H. J. Org. Chem. 1998, 63, 824-832. For application of catalytic asymmetric RCM in target-oriented synthesis see: (f) Burke, S. D.; Muller, N.; Beudry, C. M. Org. Lett. 1999, 1, 1827-1829. For Mo-catalyzed asymmetric ROM reactions see: (g) La, D. S.; Ford, J. G.; Sattely, E. S.; Bonitatebus, P. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 11603-11604. (h) Reference 16f.
108. For Mo-catalyzed asymmetric RCM reactions, see: (a) Alexander, J. B.; La, D. S.; Cefalo, D. R.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 4041-4042. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720-9721. (c) Zhu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251-8259. (d) Fujimura, O.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2499-2500. (e) Fujimura, O.; Grubbs, R. H. J. Org. Chem. 1998, 63, 824-832. For application of catalytic asymmetric RCM in target- oriented synthesis see: (f) Burke, S. D.; Muller, N.; Beudry, C. M. Org. Lett. 1999, 1, 1827-1829. For Mo-catalyzed asymmetric ROM reactions see: (g) La, D. S.; Ford, J. G.; Sattely, E. S.; Bonitatebus, P. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 11603-11604. (h) Reference 16f.
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111. Grubbs and co-workers recently reported (see ref 8a) the syntheses of the first four compounds described in this Experimental Section. However, experimental details and complete characterization for all of these materials were not provided. A recent disclosure (Arduengo, A. J., III; Goerlich, J. R.; Marshall, W. J. J. Am. Chem. Soc. 1995, 117, 11027-11028) also describes 1,3-dimesitylimidazolinium chloride, but characterization is only mentioned for the corresponding 1,3-dimesitylimidazolin-2-ylidene. We have found the procedures described above satisfactory for the efficient synthesis of these materials in multigram quantities.
112. Saba, S.; Brescia, A.-M.; Kaloustain, M. K. Tetrahedron Lett. 1991, 32, 5031-5034.
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