New Alkoxysilanes for C–C Coupling Reactions

Chemfiles Volume 3 Article 5

The use of silicon compounds as transmetalation reagents has attracted much attention as a viable alternative to the popular Stille and Suzuki coupling reactions mainly due to the formation of nontoxic byproducts and stability to many reaction conditions. 1 Silicon-based coupling reactions can be carried out using aryl-, heteroaryl-, or alkenyl- halides and alkoxysilanes in the presence of palladium or rhodium catalysts. Among the various types of silicon compounds available, alkoxysilanes are more effective in coupling reactions.2

Recently, considerable attention has been paid to the rhodiumcatalyzed addition of aryl(trialkoxy)silanes to carbonyl compounds, such as aldehydes, α,β-unsaturated ketones and esters.3

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  1. (a) Hatanaka, Y.; Hiyama, T. Synlett 1991, 845. (b) Chuit, C. et al. Chem. Rev. 1993, 93, 1371. (c) Horn, K. A. ibid. 1995, 95, 1317. (d) Hiyama, T.; Shirakawa, E. In Topics of Current Chemistry; Miyaura, N., Ed.; Spinger-Verlag: Heidelberg, 2002; vol. 219, p 61.
  2. (a) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835. (b) Tamao, K. et al. Tetrahedron Lett. 1989, 30, 6051. (c) Shibata, K. et al. Chem. Commun. 1997, 1309. (d) Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684. (e) Mowery, M. E.; DeShong, P. Org. Lett. 1999, 1, 2140. (f) Lee, H. M.; Nolan, S. P. ibid. 2000, 2, 2053. (g) Murata. M. et al. Synthesis 2001, 2231.
  3. Oi, S. et al. Org. Lett. 2002, 4, 667.

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