Catalytic amide-mediated methyl transfer from silanes to alkenes in Fujiwara-Moritani oxidative coupling

Angewandte Chemie - International Edition

Volumn 47, Issue 22, 2008, Pages 4228-4230

  Rauf, Waqar ^a   Brown, John M ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

C Si activation; Fujiwara Moritani reaction; Homogeneous catalysis; Methyl transfer; Oxidative Heck coupling

Indexed keywords

AMIDES; CHEMICAL REACTIONS; HYDROCARBONS; OLEFINS; SILANES;

C-SI ACTIVATION; FUJIWARA-MORITANI REACTION; HOMOGENEOUS CATALYSIS; METHYL TRANSFER; OXIDATIVE HECK COUPLING;

ACTIVATED CARBON;

EID: 53549103595     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800815     Document Type: Article

References (27)

1. For the intramolecular case, see: L. Firmansjah, G. C. Fu, J. Am. Chem. Soc. 2007, 129, 11340-11341.
2. 4]) is longstanding: R. F. Heck, J. Am. Chem. Soc. 1968, 90, 5518-5526.
3. Recent reviews: a) O. Daugulis, V. G. Zaitsev, D. Shabashov, Q.-N. Pham, A. Lazareva, Synlett 2006, 3382-3388;
4. b) J.-Q. Yu, R. Giri, X. Chen, Org. Biomol. Chem. 2006, 4, 4041-4047;
5. c) A. Kaliyani, M. S. Sanford, Top. Organomet. Chem. 2008, 24, 85-116.
6. a) C. G. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633-639;
7. b) I. Moritani, Y. Fujiwara, Synthesis 1973, 524-533;
8. c) Y. Fujiwara, I. Moritani, S. Danno, R. Asano, S. Teranish, J. Am. Chem. Soc. 1969, 91, 7166-7169.
9. C. Eaborn, J. Organomet. Chem. 1975, 100, 43-57.
10. R. C. Larock, C. L. Liu, H. H. Lau, S. Varaprath, Tetrahedron Lett. 1984, 25, 4459-4462.
11. Stoichiometric intramolecular activation of aryl or benzyl groups in silanes by Pd salts: J. M. Valk, J. Boersma, G. Van Koten, J. Organomet. Chem. 1994, 483, 213-216.
12. a) Y. Nakao, J. Chen, M. Tanaka, T. Hiyama, J. Am. Chem. Soc. 2007, 129, 11694-11695;
13. b) Y. Nakao, H. Imanaka, A. K. Sahoo, A. Yada, T. Hiyama, J. Am. Chem. Soc. 2005, 127, 6952-6953.
14. U. C. Yoon, S. J. Cho, Y. J. Lee, M. J. Mancheno, P. S. Mariano, J. Org. Chem. 1995, 60, 2353-2360.
15. J. Y. Lequestel, C. Laurence, A. Lachkar, M. Helbert, M. Berthelot, J. Chem. Soc. Perkin Trans. 2 1992, 2091-2094.
16. Examples of urea-directed catalytic reactions: a) Z. Song, R. P. Hsung, T. Lu, A. G. Lohse, J. Org. Chem. 2007, 72, 9722-9731;
17. b) C. A. Busacca, J. C. Lorenz, N. Grinberg, N. Haddad, H. Lee, Z. Li, M. Liang, D. Reeves, A. Saha, R. Varsolona, C. H. Senanayake, Org. Lett. 2008, 10, 341-344.
18. J. Clayden, M. Dufour, Tetrahedron Lett. 2006, 47, 6945-6946.
19. From the aryl isocyanates according to: R. Laudien, R. Mitzner, Perkin Trans. 2 2001, 2226-2229.
20. See also: D. Tanaka, A. G. Myers, Org. Lett. 2004, 6, 433-436.
21. I. Moritani, Y. Fujiwara, Tetrahedron Lett. 1967, 8, 1119-1122.
22. P.-A. Enquist, P. Nilsson, P. Sjoeberg, M. Larhed, J. Org. Chem. 2006, 71, 8779-8786;
23. C. H. Yoon, K. S. Yoo, S. W. Yi, R. K. Mishra, K. W. Jung, Org. Lett. 2004, 6, 4037-4039.
24. I. S. Akhrem, N. M. Chistovalova, M. E. Volpin, Uspekhi Khimii 1983, 52, 953-975, and references therein.
25. Y. Hatanaka, T. Hiyama, Tetrahedron Lett. 1988, 29, 97-98.
26. V. V. Negrebetsky, P. G. Taylor, E. P. Kramarova, S. Y. Bylikin, I. Y. Belavin, A. G. Shipov, A. R. Bassindale, Y. I. Baukov, J. Organomet. Chem. 2006, 691, 3976-3988, and earlier papers in this series.
27. D. A. Fletcher, R. F. McMeeking, D. Parkin, J. Chem. Inf. Comput. Sci. 1996, 36, 746-749.