Novel carbon-carbon bond-forming reactions using carbocations produced from substituted propargyl silyl ethers by the action of TMSOTf

Teruhiko Ishikawa, M. Okano, T. Aikawa, S. Saito

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Abstract

Highly useful carbon-carbon bond forming reactions using stable allenyl, propargyl, or allyl-propargyl hybrid cations have been developed. These carbocations could be generated from silyl 1-(π-donor)-substituted propargyl ethers by the action of trimethylsilyl trifluoromethanesulfonate in dichloromethane at -78 °C to room temperature and could be attacked nucleophilically by electron rich arenes, allylsilanes, or enol silyl ethers, giving rise to allenes, alkynes, and their derivatives. A novel method for regio- and stereoselective synthesis of conjugated enynes utilizing allyl-propargyl hybrid cations has also been established.

Original languageEnglish
Pages (from-to)4635-4642
Number of pages8
JournalJournal of Organic Chemistry
Volume66
Issue number13
DOIs
Publication statusPublished - Jun 29 2001

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ASJC Scopus subject areas

  • Organic Chemistry

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