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Iridium-catalyzed (Z)-trialkylsilylation of Terminal Olefins

Biao Lu, J R Falck

J Org Chem. 2010 Mar 5;75(5):1701-5.

PMID: 20136153

Abstract:

A complex of commercial [Ir(OMe)(cod)](2) and 4,4-di-tert-butyl-2,2-bipyridine (dtbpy) catalyzes the Z-selective, dehydrative silylation of terminal alkenes, but not 1,2-disubstituted alkenes, with triethylsilane or benzyldimethylsilane in THF at 40 degrees C. Yields and Z-stereoselectivity were significantly improved by 2-norbornene, in contrast with other sacrificial alkenes. The reaction is compatible with many functional groups including epoxides, ketones, amides, alcohols, esters, halides, ketals, and silanes. alpha,beta-Unsaturated esters were unreactive. The reaction probably proceeds through a Heck-type mechanism.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP1631705 Benzyldimethylsilane Benzyldimethylsilane 1631-70-5 Price
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