Nickel-catalyzed allylic substitution of simple alkenes

Journal of the American Chemical Society

Volumn 132, Issue 20, 2010, Pages 6880-6881

  Matsubara, Ryosuke ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLATIONS; ALLYLIC SUBSTITUTION; ALPHA-OLEFINS; CATALYST LOADINGS; COUPLING REACTION; HIGH YIELD; NONCONJUGATED;

ETHYLENE; NICKEL ALLOYS; SUBSTITUTION REACTIONS;

HYDROCARBONS;

ALCOHOL DERIVATIVE; ALKENE; NICKEL;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; SUBSTITUTION REACTION; SYNTHESIS;

ALKENES; CATALYSIS; NICKEL;

EID: 77952578899     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja101186p     Document Type: Article

References (35)

1. Trost, B. M. and Lee, C. B. In Catalytic Asymmetric Synthesis II; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 8E, pp 593 - 650.
2. Trost, B. M. Tetrahedron 1977, 33, 2615
3. Braun, M., Meier, T., Laicher, F., Meletis, P., and Fiden, M. Adv. Synth. Catal. 2008, 350, 303
4. Zhao, X., Liu, D., Xie, F., and Zhang, W. Tetrahedron 2009, 65, 512
5. Yasui, H., Mizutani, K., Yorimitsu, H., and Oshima, K. Tetrahedron 2006, 62, 1410
6. Son, S. and Fu, G. C. J. Am. Chem. Soc. 2008, 130, 2756
7. Porcel, S., López-Carrillo, V., García-Yebra, C., and Echavarren, A. M. Angew. Chem., Int. Ed. 2008, 47, 1883
8. Nishikata, T. and Lipshutz, B. H. J. Am. Chem. Soc. 2009, 131, 12103
9. Oppolzer, W. Angew. Chem., Int. Ed. 1989, 28, 38
10. Catalytic intermolecular ASRs of conjugated alkenes leading to 1,4-dienes have been reported
11. Tsukada, N., Sato, T., and Inoue, Y. Chem. Commun. 2001, 237
12. Tsukada, N., Sato, T., and Inoue, Y. Chem. Commun. 2003, 2404
13. There are far fewer ways to make 1,4-dienes with good regio- and stereocontrol than there are to make 1,3- and 1,5-dienes
14. Trost, B. M., Probst, G. D., and Schoop, A. J. Am. Chem. Soc. 1998, 120, 9228
15. Wilson, S. R. and Zucker, P. A. J. Org. Chem. 1988, 53, 4682
16. Hilt, G., du Mesnil, F.-X., and Lüers, S. Angew. Chem., Int. Ed. 2001, 40, 387
17. Moreau, B., Wu, J. Y., and Ritter, T. Org. Lett. 2009, 11, 337
18. Morten, C. J. and Jamison, T. F. Tetrahedron 2009, 65, 6648
19. Ogoshi, S., Oka, M.-a., and Kurosawa, H. J. Am. Chem. Soc. 2004, 126, 11802
20. Ogoshi, S., Haba, T., and Ohashi, M. J. Am. Chem. Soc. 2009, 131, 10350
21. Ng, S.-S. and Jamison, T. F. J. Am. Chem. Soc. 2005, 127, 14194
22. Ho, C.-Y., Ng, S.-S., and Jamison, T. F. J. Am. Chem. Soc. 2006, 128, 5362
23. Schleicher, K. D. and Jamison, T. F. Org. Lett. 2007, 9, 875
24. Ho, C.-Y. and Jamison, T. F. Angew. Chem., Int. Ed. 2007, 46, 782
25. Ho, C.-Y., Ohmiya, H., and Jamison, T. F. Angew. Chem., Int. Ed. 2008, 47, 1893
26. Reviews: Ng, S.-S., Ho, C.-Y., Schleicher, K. D., and Jamison, T. F. Pure Appl. Chem. 2008, 80, 929
27. Ho, C.-Y., Schleicher, K. D., Chan, C.-W., and Jamison, T. F. Synlett 2009, 2565
28. Methyl acrylate did not undergo allylation with 1b.
29. The mechanism of intramolecular ASR of olefins has been thoroughly investigated.
30. Gómez-Bengoa, E., Cuerva, J. M., Echavarren, A. M., and Martorell, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 767
31. Cárdienas, D. J., Alcamí, M., Cossío, F., Méndez, M., and Echavarren, A. M. Chem. - Eur. J. 2003, 9, 96 A similar olefin insertion step has also been studied in reactions involving cationic metal hydrides
32. Mecking, S. and Keim, W. Organometallics 1996, 15, 2650
33. DiRenzo, G. M., White, P. S., and Brookhart, M. J. Am. Chem. Soc. 1996, 118, 6225
34. Joseph, J., RajanBabu, T. V., and Jemmis, E. D. Organometallics 2009, 28, 3552
35. 3SiOTf. Yamamoto, T., Ishizu, J., and Yamamoto, A. J. Am. Chem. Soc. 1981, 103, 6863