Highly efficient, reversible addition of activated methylene compounds to styrene derivatives catalyzed by silver catalysts

Journal of Organic Chemistry

Volumn 70, Issue 14, 2005, Pages 5752-5755

  Yao, Xiaoquan ^a   Li, Chao Jun ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; KETONES; OLEFINS; SILVER; STYRENE;

CARBON-CARBON BONDS; CLEAVAGE; METHYLENE COMPOUNDS;

ADDITION REACTIONS;

CARBENOID; CARBON; DIKETONE; ESTER DERIVATIVE; SILVER DERIVATIVE; SILVER TRIFLATE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYST; CHEMICAL BINDING; HIGH TEMPERATURE PROCEDURES; MOLECULAR MODEL;

EID: 22144452177     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050570n     Document Type: Article

References (30)

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. (a) Pei, T.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11290.
5. (b) Pei, T.; Widenhoefer, R. A. Chem. Commun. 2002, 650.
6. (c) Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 2056.
7. (d) Pei, T.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 648.
8. (e) Wang, X.; Pei, T.; Han, X.; Widenhoefer, R. A. Org. Lett. 2003, 5, 2699.
9. (f) Yang, D.; Li, J. H.; Gao, Q.; Yan, Y. L. Org. Lett. 2003, 5, 2869.
10. Wang, X.; Widenhoefer, R. A. Chem. Commun. 2004, 660.
11. Leitner, A.; Larsen, J.; Steffens, C.; Hartwig, J. F. J. Org. Chem. 2004, 69, 7552.
12. Yao, X. Q.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 6884.
13. Nguyen, R.-V.; Yao, X. Q. Bohle, D. S., Li, C.-J. Org. Lett. 2005, 7, 673.
14. For some recent examples, as Lewis acid: (a) Josephaohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 3734-3735.
15. (b) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5360.
16. (c) Peddibhotla, S.; Tepe, J. J. J. Am. Chem. Soc. 2004, 126, 12766.
17. Others: (d) Cirakovic, J.; Driver, T. G.; Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 9370.
18. (e) Dias, H. V. R.; Browning, R. G.; Polach, S. A.; Diyabalanage, H. V. K.; Lovely, C. J. J. Am. Chem. Soc. 2003, 125, 9270.
19. (f) Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202.
20. (g) Clark, T. B.; Woerpel, K. A. J. Am. Chem. Soc. 2004, 126, 9522.
21. (h) Dias, H. V. R.; Browning, R. G.; Richey, S. A.; Lovely, C. J. Organometallics 2004, 23, 1200.
22. (i) Cui, Y.; He, C. Angew. Chem., Int. Ed. 2004, 43, 4210.
23. (j) Driver, T. G.; Woerpel, K. A. J. Am. Chem. Soc. 2004, 126, 9993.
24. Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473.
25. Li, Z.; Wei, C.; Chen, L.; Varma, R. S.; Li, C.-J. Tetrahedron Lett. 2004, 45, 2443.
26. Very recently, a nickel-catalyzed carbon-carbon bond-cleavage reaction was reported. The substrate is very similar to 3, and the 1,3-dicarbonyl structure was needed. See: Necas, D.; Tursky, M.; Kotora, M. J. Am. Chem. Soc. 2004, 126, 10222.
27. 3/ 15 mol % of AgOTf at refluxing temperature in DCE. The ratio of the two distereomers is 39:61.
28. A similar mechanism has been studied elegantly by Reetze and co-worker in gold-catalyzed reaction of arenes with alkynes; see: (a) Reetze, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485.
29. See also: (b) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526.
30. (c) Nakamura, M.; Endo, K; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 13002. We also thank the reviewers for their suggestions regarding this mechanism.