Highly efficient addition of activated methylene compounds to alkenes catalyzed by gold and silver

Journal of the American Chemical Society

Volumn 126, Issue 22, 2004, Pages 6884-6885

  Yao, Xiaoquan ^a   Li, Chao Jun ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIKETONE; ALKENE; BETA KETONE ESTER; CARBENE; DIKETONE; GOLD; HALIDE; NITROMETHANE; PALLADIUM; RUTHENIUM; SILVER; STYRENE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ARYLATION; CATALYSIS; METHODOLOGY; STOICHIOMETRY;

EID: 3042854420     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0482637     Document Type: Article

References (37)

1. (a) Trost, B. M. Science 1991, 254, 1471.
2. (b) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
3. (c) Trost, B. M. Acc. Chem. Res. 2002, 35, 695.
4. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
5. Trost, B. M.; Imi, K.; Davies, I. J. Am. Chem. Soc. 1995, 117, 5371.
6. For reviews, see: (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
7. (b) Dyker, G. Angew. Chem. 1999, 38, 1698.
8. (c) Naota, T.; Takaya, H.; Murahashi, S. I. Chem. Rev. 1998, 98, 2599.
9. 3 C-H bonds, see: (d) Jun, C. H.; Hwang, D. C.; Na, S. J. Chem. Commun. 1998, 1405.
10. (e) Chatani, N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 10935.
11. (f) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019.
12. (g) Salter, M. M.; Gevorgyan, V.; Saito, S.; Yamamoto, Y. Chem. Commun. 1996, 17.
13. For hydrovinylation, see: (h) RajanBabu, T. V. Chem. Rev. 2003, 103, 2845.
14. (i) Goossen, L. J. Angew. Chem., int. Ed 2002, 41, 3775.
15. (a) Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 2056.
16. (b) Pei, T.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 648.
17. (c) Wang, X.; Pei, T.; Han, X.; Widenhoefer, R. A. Org. Lett. 2003, 5, 2699.
18. See also (d) Yang, D.; Li, J. H.; Gao, Q.; Yan, Y. L. Org. Lett. 2003, 5, 2869.
19. Widenhoefer very recently reported the reaction with ethylene and propene. See: (e) Wang, X.; Widenhoefer, R. A. Chem. Commun. 2004, 660.
20. (a) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215.
21. (b) Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727.
22. (a) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Catal. Today 2002, 72, 19.
23. (b) Hashmi, A. S. K.; Schwarz, L.; Choi, J. H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285.
24. (a) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett. 1996, 37, 4969.
25. (b) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650.
26. (c) Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563.
27. (d) Fuchita, Y.; Utsunomiya, Y.; Yasutaka, M. J. Chem. Soc., Dalton Trans. 2001, 2330.
28. (e) Mueller, T. E.; Grosche, M.; Herdtweck, E.; Pleier, A. K.: Walter, E.; Yan, Y. K. Organometallics 2000, 19, 170.
29. Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584.
30. (a) Wei, C. M.; Li, Z. G.; Li, C. J. Org. Lett. 2003, 5, 4473.
31. (b) Li, Z. G.; Wei, C. M.; Chen, L.; Varma, R. S.; Li, C. J. Tetrahedron Lett. 2004, 45, 2443.
32. Hashmi, A. S. K.; Ding, L.; Bats, J. W.; Fischer, P.; Frey, W. Chem.-Eur. J. 2003, 9, 4339.
33. Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485.
34. (a) Arcadi, A.; Bianchi, G.; Marinelli, F. Synthesis 2004, 610.
35. See also: (b) He, C. 227th National Meeting of the American Chemical Society, Anaheim, CA, March 28-April 1, 2004; INOR-070.
36. During the preparation of our manuscript, an intramolecular addition of 1,3-dicarbonyl compounds to alkynes was reported. See: Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527. For an indium-catalyzed addition, see: Nakamura, M.; Endo, K.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 13002.
37. During the preparation of our manuscript, an intramolecular addition of 1,3-dicarbonyl compounds to alkynes was reported. See: Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527. For an indium-catalyzed addition, see: Nakamura, M.; Endo, K.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 13002.