Highly efficient B(C6F5)3-catalyzed hydrosilylation of olefins

Michael Rubin, Todd Schwier, Vladimir Gevorgyan

Research output: Contribution to journalArticle

192 Scopus citations

Abstract

A convenient and highly efficient method for the Lewis acid-catalyzed trans-selective hydrosilylation of alkenes has been developed. The mechanism of this novel protocol operates via direct addition of silylium type species across C=C bond followed by trapping of the resultant carbenium ion with boron-bound hydride. A number of diversely substituted silanes possessing both aryl and alkyl groups at silicon atom were efficiently prepared using this hydrosilylation methodology. The possibility to employ aryl-containing hydrosilanes in this reaction opens broad capabilities for the synthesis of alcohols via a trans-selective hydrosilylation/Tamao - Fleming oxidation sequence, complementary to the existing cis-selective hydroboration/oxidation protocol.

Original languageEnglish (US)
Pages (from-to)1936-1940
Number of pages5
JournalJournal of Organic Chemistry
Volume67
Issue number6
DOIs
StatePublished - Mar 22 2002
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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