Palladium-tetraphosphine complex: An efficient catalyst for the alkynylation of ortho-substituted aryl bromides

Synthesis

Volumn , Issue 8, 2004, Pages 1281-1289

  Feuerstein, Marie ^a   Berthiol, Florian ^a   Doucet, Henri ^a   Santelli, Maurice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Alkynes; Alkynylation; Aryl bromides; Catalysis; Palladium; Tetraphosphine

Indexed keywords

AROMATIC COMPOUNDS; BROMINE COMPOUNDS; CATALYSTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ALKYNYLATION; TETRAPHOSPHINE;

PALLADIUM COMPOUNDS;

ACETIC ACID DERIVATIVE; ACETOPHENONE DERIVATIVE; ACETYLENE DERIVATIVE; ANISOLE DERIVATIVE; ANTHRACENE DERIVATIVE; BENZALDEHYDE DERIVATIVE; BENZENE DERIVATIVE; BENZONITRILE; BIPHENYL DERIVATIVE; BROMINE DERIVATIVE; BUTANE; CYCLOPENTANE DERIVATIVE; FLUOROFORM; INDOLE DERIVATIVE; NAPHTHALENE DERIVATIVE; NITRILE; PALLADIUM COMPLEX; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TOLUENE DERIVATIVE;

ALKYNYLATION; ARTICLE; CATALYSIS; HECK REACTION; SUBSTITUTION REACTION;

EID: 2942739442     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822354     Document Type: Article

References (46)

1. For reviews on the Pd-catalysed reaction of aryl halides with alkynes see: (a) Sonogashira, K. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998. (b) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, 1998. (c) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46.
2. For reviews on the Pd-catalysed reaction of aryl halides with alkynes see: (a) Sonogashira, K. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998. (b) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, 1998. (c) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46.
3. For reviews on the Pd-catalysed reaction of aryl halides with alkynes see: (a) Sonogashira, K. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998. (b) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, 1998. (c) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46.
4. For examples of efficient Pd-cataly sts for the alky nylation of aryl halides: (a) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (b) Nakamura, K.; Okubo, H.; Yamaguchi, M. Synlett 1999, 549. (c) Herrmann, W. A.; Böhm, V.; Reisinger, C.-P. J. Organomet. Chem. 1999, 576, 23. (d) McGuinness, D.; Cavell, K. Organometallics 2000, 19, 741. (e) Buchmeiser, M.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39. (f) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411. (g) Yang, C.; Nolan, S. Organometallics 2002, 21, 1020. (h) Méry, D.; Heuzé, K.; Astruc, D. Chem. Commun. 2003, 1934.
5. For examples of efficient Pd-cataly sts for the alky nylation of aryl halides: (a) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (b) Nakamura, K.; Okubo, H.; Yamaguchi, M. Synlett 1999, 549. (c) Herrmann, W. A.; Böhm, V.; Reisinger, C.-P. J. Organomet. Chem. 1999, 576, 23. (d) McGuinness, D.; Cavell, K. Organometallics 2000, 19, 741. (e) Buchmeiser, M.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39. (f) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411. (g) Yang, C.; Nolan, S. Organometallics 2002, 21, 1020. (h) Méry, D.; Heuzé, K.; Astruc, D. Chem. Commun. 2003, 1934.
6. For examples of efficient Pd-cataly sts for the alky nylation of aryl halides: (a) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (b) Nakamura, K.; Okubo, H.; Yamaguchi, M. Synlett 1999, 549. (c) Herrmann, W. A.; Böhm, V.; Reisinger, C.-P. J. Organomet. Chem. 1999, 576, 23. (d) McGuinness, D.; Cavell, K. Organometallics 2000, 19, 741. (e) Buchmeiser, M.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39. (f) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411. (g) Yang, C.; Nolan, S. Organometallics 2002, 21, 1020. (h) Méry, D.; Heuzé, K.; Astruc, D. Chem. Commun. 2003, 1934.
7. For examples of efficient Pd-cataly sts for the alky nylation of aryl halides: (a) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (b) Nakamura, K.; Okubo, H.; Yamaguchi, M. Synlett 1999, 549. (c) Herrmann, W. A.; Böhm, V.; Reisinger, C.-P. J. Organomet. Chem. 1999, 576, 23. (d) McGuinness, D.; Cavell, K. Organometallics 2000, 19, 741. (e) Buchmeiser, M.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39. (f) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411. (g) Yang, C.; Nolan, S. Organometallics 2002, 21, 1020. (h) Méry, D.; Heuzé, K.; Astruc, D. Chem. Commun. 2003, 1934.
8. For examples of efficient Pd-cataly sts for the alky nylation of aryl halides: (a) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (b) Nakamura, K.; Okubo, H.; Yamaguchi, M. Synlett 1999, 549. (c) Herrmann, W. A.; Böhm, V.; Reisinger, C.-P. J. Organomet. Chem. 1999, 576, 23. (d) McGuinness, D.; Cavell, K. Organometallics 2000, 19, 741. (e) Buchmeiser, M.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39. (f) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411. (g) Yang, C.; Nolan, S. Organometallics 2002, 21, 1020. (h) Méry, D.; Heuzé, K.; Astruc, D. Chem. Commun. 2003, 1934.
9. For examples of efficient Pd-cataly sts for the alky nylation of aryl halides: (a) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (b) Nakamura, K.; Okubo, H.; Yamaguchi, M. Synlett 1999, 549. (c) Herrmann, W. A.; Böhm, V.; Reisinger, C.-P. J. Organomet. Chem. 1999, 576, 23. (d) McGuinness, D.; Cavell, K. Organometallics 2000, 19, 741. (e) Buchmeiser, M.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39. (f) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411. (g) Yang, C.; Nolan, S. Organometallics 2002, 21, 1020. (h) Méry, D.; Heuzé, K.; Astruc, D. Chem. Commun. 2003, 1934.
10. For examples of efficient Pd-cataly sts for the alky nylation of aryl halides: (a) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (b) Nakamura, K.; Okubo, H.; Yamaguchi, M. Synlett 1999, 549. (c) Herrmann, W. A.; Böhm, V.; Reisinger, C.-P. J. Organomet. Chem. 1999, 576, 23. (d) McGuinness, D.; Cavell, K. Organometallics 2000, 19, 741. (e) Buchmeiser, M.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39. (f) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411. (g) Yang, C.; Nolan, S. Organometallics 2002, 21, 1020. (h) Méry, D.; Heuzé, K.; Astruc, D. Chem. Commun. 2003, 1934.
11. For examples of efficient Pd-cataly sts for the alky nylation of aryl halides: (a) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (b) Nakamura, K.; Okubo, H.; Yamaguchi, M. Synlett 1999, 549. (c) Herrmann, W. A.; Böhm, V.; Reisinger, C.-P. J. Organomet. Chem. 1999, 576, 23. (d) McGuinness, D.; Cavell, K. Organometallics 2000, 19, 741. (e) Buchmeiser, M.; Schareina, T.; Kempe, R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39. (f) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411. (g) Yang, C.; Nolan, S. Organometallics 2002, 21, 1020. (h) Méry, D.; Heuzé, K.; Astruc, D. Chem. Commun. 2003, 1934.
12. 3 as ligand: (a) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. (b) Makra, F.; Rohloff, J. C.; Muehldorf, A. V.; Link, J. O. Tetrahedron Lett. 1995, 46, 6815. (c) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109. (d) Pschirer, N. G.; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481. (e) Dyker, G.; Stirner, W.; Henkel, G. Eur. J. Org. Chem. 2000, 1433. (f) Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Tetrahedron Lett. 2000, 41, 5151. (g) Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T. Tetrahedron 2001, 57, 9697. (h) Mori A.; Shimada, T.; Kondo, T.: Sekiguchi, A. Synlett 2001, 649. (i) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017. (j) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86. (k) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
13. 3 as ligand: (a) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. (b) Makra, F.; Rohloff, J. C.; Muehldorf, A. V.; Link, J. O. Tetrahedron Lett. 1995, 46, 6815. (c) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109. (d) Pschirer, N. G.; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481. (e) Dyker, G.; Stirner, W.; Henkel, G. Eur. J. Org. Chem. 2000, 1433. (f) Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Tetrahedron Lett. 2000, 41, 5151. (g) Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T. Tetrahedron 2001, 57, 9697. (h) Mori A.; Shimada, T.; Kondo, T.: Sekiguchi, A. Synlett 2001, 649. (i) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017. (j) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86. (k) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
14. 3 as ligand: (a) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. (b) Makra, F.; Rohloff, J. C.; Muehldorf, A. V.; Link, J. O. Tetrahedron Lett. 1995, 46, 6815. (c) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109. (d) Pschirer, N. G.; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481. (e) Dyker, G.; Stirner, W.; Henkel, G. Eur. J. Org. Chem. 2000, 1433. (f) Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Tetrahedron Lett. 2000, 41, 5151. (g) Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T. Tetrahedron 2001, 57, 9697. (h) Mori A.; Shimada, T.; Kondo, T.: Sekiguchi, A. Synlett 2001, 649. (i) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017. (j) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86. (k) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
15. 3 as ligand: (a) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. (b) Makra, F.; Rohloff, J. C.; Muehldorf, A. V.; Link, J. O. Tetrahedron Lett. 1995, 46, 6815. (c) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109. (d) Pschirer, N. G.; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481. (e) Dyker, G.; Stirner, W.; Henkel, G. Eur. J. Org. Chem. 2000, 1433. (f) Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Tetrahedron Lett. 2000, 41, 5151. (g) Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T. Tetrahedron 2001, 57, 9697. (h) Mori A.; Shimada, T.; Kondo, T.: Sekiguchi, A. Synlett 2001, 649. (i) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017. (j) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86. (k) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
16. 3 as ligand: (a) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. (b) Makra, F.; Rohloff, J. C.; Muehldorf, A. V.; Link, J. O. Tetrahedron Lett. 1995, 46, 6815. (c) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109. (d) Pschirer, N. G.; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481. (e) Dyker, G.; Stirner, W.; Henkel, G. Eur. J. Org. Chem. 2000, 1433. (f) Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Tetrahedron Lett. 2000, 41, 5151. (g) Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T. Tetrahedron 2001, 57, 9697. (h) Mori A.; Shimada, T.; Kondo, T.: Sekiguchi, A. Synlett 2001, 649. (i) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017. (j) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86. (k) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
17. 3 as ligand: (a) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. (b) Makra, F.; Rohloff, J. C.; Muehldorf, A. V.; Link, J. O. Tetrahedron Lett. 1995, 46, 6815. (c) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109. (d) Pschirer, N. G.; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481. (e) Dyker, G.; Stirner, W.; Henkel, G. Eur. J. Org. Chem. 2000, 1433. (f) Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Tetrahedron Lett. 2000, 41, 5151. (g) Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T. Tetrahedron 2001, 57, 9697. (h) Mori A.; Shimada, T.; Kondo, T.: Sekiguchi, A. Synlett 2001, 649. (i) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017. (j) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86. (k) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
18. 3 as ligand: (a) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. (b) Makra, F.; Rohloff, J. C.; Muehldorf, A. V.; Link, J. O. Tetrahedron Lett. 1995, 46, 6815. (c) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109. (d) Pschirer, N. G.; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481. (e) Dyker, G.; Stirner, W.; Henkel, G. Eur. J. Org. Chem. 2000, 1433. (f) Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Tetrahedron Lett. 2000, 41, 5151. (g) Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T. Tetrahedron 2001, 57, 9697. (h) Mori A.; Shimada, T.; Kondo, T.: Sekiguchi, A. Synlett 2001, 649. (i) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017. (j) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86. (k) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
19. 3 as ligand: (a) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. (b) Makra, F.; Rohloff, J. C.; Muehldorf, A. V.; Link, J. O. Tetrahedron Lett. 1995, 46, 6815. (c) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109. (d) Pschirer, N. G.; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481. (e) Dyker, G.; Stirner, W.; Henkel, G. Eur. J. Org. Chem. 2000, 1433. (f) Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Tetrahedron Lett. 2000, 41, 5151. (g) Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T. Tetrahedron 2001, 57, 9697. (h) Mori A.; Shimada, T.; Kondo, T.: Sekiguchi, A. Synlett 2001, 649. (i) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017. (j) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86. (k) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
20. 3 as ligand: (a) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. (b) Makra, F.; Rohloff, J. C.; Muehldorf, A. V.; Link, J. O. Tetrahedron Lett. 1995, 46, 6815. (c) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109. (d) Pschirer, N. G.; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481. (e) Dyker, G.; Stirner, W.; Henkel, G. Eur. J. Org. Chem. 2000, 1433. (f) Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Tetrahedron Lett. 2000, 41, 5151. (g) Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T. Tetrahedron 2001, 57, 9697. (h) Mori A.; Shimada, T.; Kondo, T.: Sekiguchi, A. Synlett 2001, 649. (i) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017. (j) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86. (k) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
21. 3 as ligand: (a) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. (b) Makra, F.; Rohloff, J. C.; Muehldorf, A. V.; Link, J. O. Tetrahedron Lett. 1995, 46, 6815. (c) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109. (d) Pschirer, N. G.; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481. (e) Dyker, G.; Stirner, W.; Henkel, G. Eur. J. Org. Chem. 2000, 1433. (f) Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Tetrahedron Lett. 2000, 41, 5151. (g) Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T. Tetrahedron 2001, 57, 9697. (h) Mori A.; Shimada, T.; Kondo, T.: Sekiguchi, A. Synlett 2001, 649. (i) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017. (j) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86. (k) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
22. 3 as ligand: (a) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. (b) Makra, F.; Rohloff, J. C.; Muehldorf, A. V.; Link, J. O. Tetrahedron Lett. 1995, 46, 6815. (c) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109. (d) Pschirer, N. G.; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481. (e) Dyker, G.; Stirner, W.; Henkel, G. Eur. J. Org. Chem. 2000, 1433. (f) Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Tetrahedron Lett. 2000, 41, 5151. (g) Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T. Tetrahedron 2001, 57, 9697. (h) Mori A.; Shimada, T.; Kondo, T.: Sekiguchi, A. Synlett 2001, 649. (i) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017. (j) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86. (k) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
23. 3 as ligand: (a) Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803. (b) Makra, F.; Rohloff, J. C.; Muehldorf, A. V.; Link, J. O. Tetrahedron Lett. 1995, 46, 6815. (c) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109. (d) Pschirer, N. G.; Bunz, U. H. F. Tetrahedron Lett. 1999, 40, 2481. (e) Dyker, G.; Stirner, W.; Henkel, G. Eur. J. Org. Chem. 2000, 1433. (f) Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Tetrahedron Lett. 2000, 41, 5151. (g) Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T. Tetrahedron 2001, 57, 9697. (h) Mori A.; Shimada, T.; Kondo, T.: Sekiguchi, A. Synlett 2001, 649. (i) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017. (j) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86. (k) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437. (l) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
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