A highly efficient three-component coupling of aldehyde, alkyne, and amines via C-H activation catalyzed by gold in water

Journal of the American Chemical Society

Volumn 125, Issue 32, 2003, Pages 9584-9585

  Wei, Chunmei ^a,b   Li, Chao Jun ^a,b  

^a Tulane University   (Canada)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; BENZALDEHYDE DERIVATIVE; GOLD; PIPERIDINE DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 0042125406     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0359299     Document Type: Article

References (42)

1. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford 1998.
2. Li, C. J. Tetrahedron 1996, 52, 5643; Chan, T. H.; Isaac, M. B. Pure Appl. Chem. 1996, 68, 919; Li, C. J: Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: Glasgow, 1998; Li, C. J. Chem. Rev. 1993, 93, 2023; Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
3. Li, C. J. Tetrahedron 1996, 52, 5643; Chan, T. H.; Isaac, M. B. Pure Appl. Chem. 1996, 68, 919; Li, C. J: Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: Glasgow, 1998; Li, C. J. Chem. Rev. 1993, 93, 2023; Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
4. Li, C. J. Tetrahedron 1996, 52, 5643; Chan, T. H.; Isaac, M. B. Pure Appl. Chem. 1996, 68, 919; Li, C. J: Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: Glasgow, 1998; Li, C. J. Chem. Rev. 1993, 93, 2023; Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
5. Li, C. J. Tetrahedron 1996, 52, 5643; Chan, T. H.; Isaac, M. B. Pure Appl. Chem. 1996, 68, 919; Li, C. J: Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: Glasgow, 1998; Li, C. J. Chem. Rev. 1993, 93, 2023; Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
6. Li, C. J. Tetrahedron 1996, 52, 5643; Chan, T. H.; Isaac, M. B. Pure Appl. Chem. 1996, 68, 919; Li, C. J: Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: Glasgow, 1998; Li, C. J. Chem. Rev. 1993, 93, 2023; Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
7. Li, C. J. Tetrahedron 1996, 52, 5643; Chan, T. H.; Isaac, M. B. Pure Appl. Chem. 1996, 68, 919; Li, C. J: Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997; Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: Glasgow, 1998; Li, C. J. Chem. Rev. 1993, 93, 2023; Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
8. Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191.
9. Issac, M. B.; Chan, T. H. J. Chem. Soc., Chem. Commun. 1995, 1003; Yi, X. H.; Meng, Y.; Li, C. J. Chem. Commun. 1998, 449.
10. Issac, M. B.; Chan, T. H. J. Chem. Soc., Chem. Commun. 1995, 1003; Yi, X. H.; Meng, Y.; Li, C. J. Chem. Commun. 1998, 449.
11. Bieber, L. W.; Storch, E. C.; Malvestiti, I.; Sila, M. F. Tetrahedron Lett. 1998, 39, 9393.
12. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445; Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450; Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976; Li, C. J.; Meng, Y. J Am. Chem. Soc. 2000, 122, 9538.
13. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445; Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450; Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976; Li, C. J.; Meng, Y. J Am. Chem. Soc. 2000, 122, 9538.
14. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445; Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450; Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976; Li, C. J.; Meng, Y. J Am. Chem. Soc. 2000, 122, 9538.
15. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445; Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450; Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976; Li, C. J.; Meng, Y. J Am. Chem. Soc. 2000, 122, 9538.
16. Chan, T. H.; Li, C. J.; Wei, Z. Y. J. Chem. Soc., Chem. Commun 1990, 505.
17. Keh, C. C. K.; Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 4062; Huang, T. S.; Keh, C. C. K.; Li, C. J. Chem. Commun. 2002, 2440; Miyabe, H.; Ueda, M.; Nishimura, A.; Naito, T. Org. Lett. 2002, 4, 131.
18. Keh, C. C. K.; Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 4062; Huang, T. S.; Keh, C. C. K.; Li, C. J. Chem. Commun. 2002, 2440; Miyabe, H.; Ueda, M.; Nishimura, A.; Naito, T. Org. Lett. 2002, 4, 131.
19. Keh, C. C. K.; Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 4062; Huang, T. S.; Keh, C. C. K.; Li, C. J. Chem. Commun. 2002, 2440; Miyabe, H.; Ueda, M.; Nishimura, A.; Naito, T. Org. Lett. 2002, 4, 131.
20. For an excellent recent review, see: Naota, I.; Takaya, H.; Murahashi, S. I. Chem. Rev. 1998, 98, 2599; Dyker, G. Angew. Chem. 1999, 38, 1698.
21. For an excellent recent review, see: Naota, I.; Takaya, H.; Murahashi, S. I. Chem. Rev. 1998, 98, 2599; Dyker, G. Angew. Chem. 1999, 38, 1698.
22. Trost, B. M. Science 1991, 254, 1471.
23. Li, C. J. Acc. Chem. Res. 2002, 35, 533; Wei, C. M.; Li, C. J. Green Chem. 2002, 4, 39; Li, C. J.; Wei, C. M. Chem. Commun. 2002, 268; Zhang, J. H.; Wei, C. M.; Li, C. J. Tetrahedron Lett. 2002, 43, 5731.
24. Li, C. J. Acc. Chem. Res. 2002, 35, 533; Wei, C. M.; Li, C. J. Green Chem. 2002, 4, 39; Li, C. J.; Wei, C. M. Chem. Commun. 2002, 268; Zhang, J. H.; Wei, C. M.; Li, C. J. Tetrahedron Lett. 2002, 43, 5731.
25. Li, C. J. Acc. Chem. Res. 2002, 35, 533; Wei, C. M.; Li, C. J. Green Chem. 2002, 4, 39; Li, C. J.; Wei, C. M. Chem. Commun. 2002, 268; Zhang, J. H.; Wei, C. M.; Li, C. J. Tetrahedron Lett. 2002, 43, 5731.
26. Li, C. J. Acc. Chem. Res. 2002, 35, 533; Wei, C. M.; Li, C. J. Green Chem. 2002, 4, 39; Li, C. J.; Wei, C. M. Chem. Commun. 2002, 268; Zhang, J. H.; Wei, C. M.; Li, C. J. Tetrahedron Lett. 2002, 43, 5731.
27. Carreira, E. M. Acc. Chem. Res. 2000, 33, 373 and references therein; see also: Lu, G.; Li, X.; Chan, W. L.; Chan, A. S. C. Chem. Commun. 2002, 172; Chen, Z. L.; Xiong, W. N.; Jiang, B. Chem. Commun. 2002, 2098; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535.
28. Carreira, E. M. Acc. Chem. Res. 2000, 33, 373 and references therein; see also: Lu, G.; Li, X.; Chan, W. L.; Chan, A. S. C. Chem. Commun. 2002, 172; Chen, Z. L.; Xiong, W. N.; Jiang, B. Chem. Commun. 2002, 2098; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535.
29. Carreira, E. M. Acc. Chem. Res. 2000, 33, 373 and references therein; see also: Lu, G.; Li, X.; Chan, W. L.; Chan, A. S. C. Chem. Commun. 2002, 172; Chen, Z. L.; Xiong, W. N.; Jiang, B. Chem. Commun. 2002, 2098; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535.
30. Carreira, E. M. Acc. Chem. Res. 2000, 33, 373 and references therein; see also: Lu, G.; Li, X.; Chan, W. L.; Chan, A. S. C. Chem. Commun. 2002, 172; Chen, Z. L.; Xiong, W. N.; Jiang, B. Chem. Commun. 2002, 2098; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535.
31. Li, C. J.; Wei, C. M. J. Am. Chem. Soc. 2002, 124, 5638.
32. Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215; Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727.
33. Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215; Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727.
34. Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Catal. Today 2002, 72, 19; Hashmi, A. S. K.; Schwarz, L.; Choi, J. H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285; Hashmi, A. S. K. Gold Bull. 2003, 36, 3.
35. Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Catal. Today 2002, 72, 19; Hashmi, A. S. K.; Schwarz, L.; Choi, J. H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285; Hashmi, A. S. K. Gold Bull. 2003, 36, 3.
36. Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Catal. Today 2002, 72, 19; Hashmi, A. S. K.; Schwarz, L.; Choi, J. H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285; Hashmi, A. S. K. Gold Bull. 2003, 36, 3.
37. Hayashi, T.; Kishi E.; Soloshonok, V. A.; Uozumi Y. Tetrahedron Lett. 1996, 37, 4969; Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650; Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563; Fuchita, Y.; Utsunomiya, Y.; Yasutaka, M. J Chem. Soc., Dalton Trans. 2001, 2330; Mueller, T. E.; Grosche, M.; Herdtweck, E.; Pleier, A. K.; Walter, E.; Yan, Y. K. Organometallics 2000, 19, 170.
38. Hayashi, T.; Kishi E.; Soloshonok, V. A.; Uozumi Y. Tetrahedron Lett. 1996, 37, 4969; Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650; Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563; Fuchita, Y.; Utsunomiya, Y.; Yasutaka, M. J Chem. Soc., Dalton Trans. 2001, 2330; Mueller, T. E.; Grosche, M.; Herdtweck, E.; Pleier, A. K.; Walter, E.; Yan, Y. K. Organometallics 2000, 19, 170.
39. Hayashi, T.; Kishi E.; Soloshonok, V. A.; Uozumi Y. Tetrahedron Lett. 1996, 37, 4969; Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650; Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563; Fuchita, Y.; Utsunomiya, Y.; Yasutaka, M. J Chem. Soc., Dalton Trans. 2001, 2330; Mueller, T. E.; Grosche, M.; Herdtweck, E.; Pleier, A. K.; Walter, E.; Yan, Y. K. Organometallics 2000, 19, 170.
40. Hayashi, T.; Kishi E.; Soloshonok, V. A.; Uozumi Y. Tetrahedron Lett. 1996, 37, 4969; Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650; Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563; Fuchita, Y.; Utsunomiya, Y.; Yasutaka, M. J. Chem. Soc., Dalton Trans. 2001, 2330; Mueller, T. E.; Grosche, M.; Herdtweck, E.; Pleier, A. K.; Walter, E.; Yan, Y. K. Organometallics 2000, 19, 170.
41. Hayashi, T.; Kishi E.; Soloshonok, V. A.; Uozumi Y. Tetrahedron Lett. 1996, 37, 4969; Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650; Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563; Fuchita, Y.; Utsunomiya, Y.; Yasutaka, M. J Chem. Soc., Dalton Trans. 2001, 2330; Mueller, T. E.; Grosche, M.; Herdtweck, E.; Pleier, A. K.; Walter, E.; Yan, Y. K. Organometallics 2000, 19, 170.
42. For synthesizing alkynyl gold complexes, see: Vicente, J.; Chicote, M. T.; Abrisqueta, M. D. J. Chem. Soc., Dalton Trans. 1995, 497.