Iridium-catalyzed (Z)-trialkylsilylation of terminal olefins

Biao Lu, J. R. Falck

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

(Chemical equation presented) 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 °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. α, β-Unsaturated esters were unreactive. The reaction probably proceeds through a Heck-type mechanism.

Original languageEnglish (US)
Pages (from-to)1701-1705
Number of pages5
JournalJournal of Organic Chemistry
Volume75
Issue number5
DOIs
StatePublished - Mar 5 2010

ASJC Scopus subject areas

  • Organic Chemistry

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