Preparation, Reactivity, and Structural Peculiarities of Hydroxyalkyl-Functionalized "Second-Generation" Ruthenium Carbene Complexes

Organometallics

Volumn 23, Issue 2, 2004, Pages 280-287

  Prühs, Stefan ^a   Lehmann, Christian W ^a   Fürstner, Alois ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; CATALYSIS; CHROMATOGRAPHIC ANALYSIS; CRYSTAL STRUCTURE; IONIZATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITIVE IONS; RUTHENIUM COMPOUNDS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS; TOLUENE; X RAY CRYSTALLOGRAPHY;

DONOR/ACCEPTOR INTERACTION; FLASH CHROMATOGRAPHY;

ORGANOMETALLICS;

EID: 0942299066     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0342006     Document Type: Article

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32. The immobilization of ruthenium carbene complexes has previously been carried out mainly via the (hemi)labile Jigands in an attempt to combine the advantages of homogeneous and heterogeneous catalysis into a single manifold ("release-capture" or "boomerang" mechanism), cf. ref 11. Only a few examples of ruthenium carbene complexes immobilized through the kinetically more inert NHC- or the anionic ligands have been reported in the literature, cf.: (a) Schürer, S. C.; Gessler, S.; Buschmann, N.; Blechert, S. Angew. Chem. 2000, 112, 4062; Angew. Chem., Int. Ed. 2000, 39, 3898. (b) Mayr, M.; Mayr, B.; Buchmeiser, M. R. Angew. Chem. 2001, 113, 3957; Angew. Chem., Int. Ed. 2001, 40, 3839. (c) Krause, J. O.; Lubbad, S.; Nuyken, O.; Buchmeiser, M. R. Adv. Synth. Catal. 2003, 345, 996.
33. The immobilization of ruthenium carbene complexes has previously been carried out mainly via the (hemi)labile Jigands in an attempt to combine the advantages of homogeneous and heterogeneous catalysis into a single manifold ("release-capture" or "boomerang" mechanism), cf. ref 11. Only a few examples of ruthenium carbene complexes immobilized through the kinetically more inert NHC- or the anionic ligands have been reported in the literature, cf.: (a) Schürer, S. C.; Gessler, S.; Buschmann, N.; Blechert, S. Angew. Chem. 2000, 112, 4062; Angew. Chem., Int. Ed. 2000, 39, 3898. (b) Mayr, M.; Mayr, B.; Buchmeiser, M. R. Angew. Chem. 2001, 113, 3957; Angew. Chem., Int. Ed. 2001, 40, 3839. (c) Krause, J. O.; Lubbad, S.; Nuyken, O.; Buchmeiser, M. R. Adv. Synth. Catal. 2003, 345, 996.
34. The immobilization of ruthenium carbene complexes has previously been carried out mainly via the (hemi)labile Jigands in an attempt to combine the advantages of homogeneous and heterogeneous catalysis into a single manifold ("release-capture" or "boomerang" mechanism), cf. ref 11. Only a few examples of ruthenium carbene complexes immobilized through the kinetically more inert NHC- or the anionic ligands have been reported in the literature, cf.: (a) Schürer, S. C.; Gessler, S.; Buschmann, N.; Blechert, S. Angew. Chem. 2000, 112, 4062; Angew. Chem., Int. Ed. 2000, 39, 3898. (b) Mayr, M.; Mayr, B.; Buchmeiser, M. R. Angew. Chem. 2001, 113, 3957; Angew. Chem., Int. Ed. 2001, 40, 3839. (c) Krause, J. O.; Lubbad, S.; Nuyken, O.; Buchmeiser, M. R. Adv. Synth. Catal. 2003, 345, 996.
35. The immobilization of ruthenium carbene complexes has previously been carried out mainly via the (hemi)labile Jigands in an attempt to combine the advantages of homogeneous and heterogeneous catalysis into a single manifold ("release-capture" or "boomerang" mechanism), cf. ref 11. Only a few examples of ruthenium carbene complexes immobilized through the kinetically more inert NHC- or the anionic ligands have been reported in the literature, cf.: (a) Schürer, S. C.; Gessler, S.; Buschmann, N.; Blechert, S. Angew. Chem. 2000, 112, 4062; Angew. Chem., Int. Ed. 2000, 39, 3898. (b) Mayr, M.; Mayr, B.; Buchmeiser, M. R. Angew. Chem. 2001, 113, 3957; Angew. Chem., Int. Ed. 2001, 40, 3839. (c) Krause, J. O.; Lubbad, S.; Nuyken, O.; Buchmeiser, M. R. Adv. Synth. Catal. 2003, 345, 996.
36. The immobilization of ruthenium carbene complexes has previously been carried out mainly via the (hemi)labile Jigands in an attempt to combine the advantages of homogeneous and heterogeneous catalysis into a single manifold ("release-capture" or "boomerang" mechanism), cf. ref 11. Only a few examples of ruthenium carbene complexes immobilized through the kinetically more inert NHC- or the anionic ligands have been reported in the literature, cf.: (a) Schürer, S. C.; Gessler, S.; Buschmann, N.; Blechert, S. Angew. Chem. 2000, 112, 4062; Angew. Chem., Int. Ed. 2000, 39, 3898. (b) Mayr, M.; Mayr, B.; Buchmeiser, M. R. Angew. Chem. 2001, 113, 3957; Angew. Chem., Int. Ed. 2001, 40, 3839. (c) Krause, J. O.; Lubbad, S.; Nuyken, O.; Buchmeiser, M. R. Adv. Synth. Catal. 2003, 345, 996.
37. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
38. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
39. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
40. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
41. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
42. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
43. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
44. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
45. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
46. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
47. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
48. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
49. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
50. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
51. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
52. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
53. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
54. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
55. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
56. See the following for leading references on other types of immobilized catalysts: (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195. (b) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (c) Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc. 2003, 125, 9248. (d) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168. (e) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem. 2001, 113, 4381; Angew. Chem., Int. Ed. 2001, 40, 4251. (f) Yao, Q. Angew. Chem. 2000, 112, 4060; Angew. Chem., Int. Ed. 2000, 39, 3896. (g) Jafarpour, L.; Heck, M.-P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671. (h) Dowden, J.; Savovic, J. Chem. Commun. 2001, 37. (i) Wijkens, P.; Jastrzebski, J. T. B. H.; van der Schaaf, P. A.; Kolly, R.; Hafner, A.; van Koten, G. Org. Lett. 2000, 2, 1621. (j) Randl, S.; Buschmann, N.; Connon, S. J. ; Blechert, S. Synlett 2001, 1547. (k) Connon, S. J.; Blechert, S. Bioorg. Med. Chem. Lett. 2002. 12, 1873. (l) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem. 2002, 114, 3989; Angew. Chem., Int. Ed. 2002, 41, 3835. (m) Melis, K.; de Vos, D.; Jacobs, P.; Verpoort, F. J. Mol. Catal. A: Chem. 2001, 169, 47. (n) Akiyama, R.; Kobayashi, S. Angew. Chem. 2002, 114, 2714; Angew. Chem., Int. Ed. 2002, 41, 2602. (o) Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055. (p) Varray, S.; Lazaro, R.; Martinez, J.; Lamaty, F. Organometallics 2003, 22, 2426.
57. For Pd-NHC complexes with hydroxyalkyl side chains and their immobilization see: Schwarz, J.; Böhm, V. P. W.; Gardiner, M. G.; Grosche, M.; Herrmann, W. A.; Hieringer, W.; Raudaschl-Sieber, G. Chem. Eur. J. 2000, 6, 1773.
58. Fürstner, A.; Thiel, O. R.; Lehmann, C. W. Organometallics 2002, 21, 331-335.
59. Love, J. A.; Sanford, M. S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 10103.
60. These values are similar to those reported for an asymmetrically substituted NHC with a tert-butyldimethylsilyloxyethyl group on one of its N-substituents, cf. ref 7.
61. Determined as described in: Gould, R. O.; Gray, A. M.; Taylor, P.; Walkinshaw, M. D. J. Am. Chem. Soc. 1985, 107, 5923.
62. Aullón, G.; Bellamy, D.; Brammer, L.; Bruton, E. A.; Orpen, A. G. Chem. Commun. 1998, 653.
63. Pfleiderer, B.; Albert, K.; Bayer, E. J. Chromatogr. 1990, 506, 343.
64. In an experiment using 5 mol % of the immobilized ruthenium complex, analyses (flame ionization detection) show a ruthenium content of only ∼250 ppm in the crude product prior to flash chromatography. Thus, ca. 99% of the ruthenium initially used is removed by simple filtration.
65. (a) It has recently been shown that tethered phenols are able to undergo such intramolecular substitution reactions, cf.: van Veldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954. (b) See also: Coalter, J. N.; Huffman, J. C.; Caulton, K. G. Chem. Commun. 2001, 1158.
66. (a) It has recently been shown that tethered phenols are able to undergo such intramolecular substitution reactions, cf.: van Veldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954. (b) See also: Coalter, J. N.; Huffman, J. C.; Caulton, K. G. Chem. Commun. 2001, 1158.
67. The average ruthenium-phosphorus distance in compounds with a trans Cl-Ru-P arrangement, however, is even shorter (2.290 A), while the corresponding cis geometry has an average Ru-P bond length of 2,336 Å. These values are statistical averages obtained by analyzing 189 and 2025 corresponding bond lengths found in the CSD.
68. P,H, cf.: Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887.
69. 4, or TMSOTf led to decomposition of the starting complex only.
70. (a) Hansen, S. M.; Volland, M. A. O.; Rominger, F.; Eisenträger, F. ; Hofmann, P. Angew. Chem. 1999, 111, 1360; Angew. Chem., Int. Ed. 1999, 38, 1273.
71. (a) Hansen, S. M.; Volland, M. A. O.; Rominger, F.; Eisenträger, F. ; Hofmann, P. Angew. Chem. 1999, 111, 1360; Angew. Chem., Int. Ed. 1999, 38, 1273.
72. (b) Hansen, S. M.; Rominger, F.; Metz, M.; Hofmann, P. Chem. Eur. J. 1999, 5, 557.
73. (c) Volland, M. A. O.; Straub, B. F.; Gruber, I.; Rominger, F.; Hofmann, P. J. Organomet. Chem. 2001, 617-618, 288.
74. We are aware of only one example in which a ruthenium carbene complex bearing nonchelating ligands crystallizes with its neutral ligands being cis disposed. This complex is phosphine free and bears two pentafluorophenoxide moieties instead of the chloride ligands, cf.: Conrad, J. C.; Amoroso, D.; Czechura, P.; Yap, G. P. A.; Fogg, D. E. Organometallics 2003, 22, 3634.
75. (a) Dinger, M. B.; Mol, J. C. Organometallics 2003, 22, 1089.
76. (b) Dinger, M. B.; Mol, J. C. Eur. J. Inorg. Chem. 2003, 2827.
77. (c) Werner, H.; Grünwaid, C.; Stüer, W.; Wolf, J. Organometallics 2003, 22, 1558.
78. 8 at 80°C for 2 h re-converts it into the irons analogue 8b; however, traces of unidentified decomposition products (ca. 10%) are also detected.
79. On treatment with certain aryloxides, ruthenium carbene complexes are prone to loss of one chloride ligand and the benzylidene proton to give the corresponding alkylidyne complexes, of. ref 25 and the following: (a) Coalter, J. N.; Bollinger, J. C.; Eisenstein, O.; Caulton, K. G. New J. Chem. 2000, 24, 925. (b) See also: Lynn, D. M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 3187.
80. On treatment with certain aryloxides, ruthenium carbene complexes are prone to loss of one chloride ligand and the benzylidene proton to give the corresponding alkylidyne complexes, of. ref 25 and the following: (a) Coalter, J. N.; Bollinger, J. C.; Eisenstein, O.; Caulton, K. G. New J. Chem. 2000, 24, 925. (b) See also: Lynn, D. M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 3187.
81. For a study on the preparation and catalytic activity of neutral pyridine adducts of "second-generation" ruthenium carbene complexes see: Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 4035-4037.
82. 3)Ru-CHPh, which is also devoid of catalytic activity in standard metathesis experiments, cf.: Sanford, M. S.; Henling, L. M.; Day, M. W.; Grubbs, R. H. Angew. Chem. 2000, 112, 3593; Angew. Chem., Int. Ed. 2000, 39, 3451.
83. 3)Ru-CHPh, which is also devoid of catalytic activity in standard metathesis experiments, cf.: Sanford, M. S.; Henling, L. M.; Day, M. W.; Grubbs, R. H. Angew. Chem. 2000, 112, 3593; Angew. Chem., Int. Ed. 2000, 39, 3451.