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Iridium-Catalyzed (Z)-Trialkylsilylation of Terminal Olefins

Biao Lu and J. R. Falck*

*Departments of Biochemistry and Pharmacology, University of Texas Southwestern Medical Center, Dallas, Texas 75390, Email: j.falckutsouthwestern.edu

B. Lu, J. R. Falck, J. Org. Chem., 2010, 75, 1701-1705.

DOI: 10.1021/jo902678p


Abstract

A complex of [Ir(OMe)(cod)]2 and 4,4-di-tert-butyl-2,2-bipyridine (dtbpy) catalyzes the Z-selective, dehydrogenative silylation of terminal alkenes, but not internal alkenes, with triethylsilane or benzyldimethylsilane in THF. Yields and Z-stereoselectivity were significantly improved by 2-norbornene as sacrificial alkene. The reaction tolerates many functional groups.

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Key Words

Vinylsilanes


ID: J42-Y2010-0590