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

Research output: Contribution to journalArticle

56 Citations (Scopus)

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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Ethers
Cations
Carbon
Alkynes
Methylene Chloride
Derivatives
Electrons
Temperature
allylsilane
propadiene
trimethylsilyl trifluoromethanesulfonate
propargyl ether

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Novel carbon-carbon bond-forming reactions using carbocations produced from substituted propargyl silyl ethers by the action of TMSOTf. / Ishikawa, Teruhiko; Okano, M.; Aikawa, T.; Saito, S.

In: Journal of Organic Chemistry, Vol. 66, No. 13, 29.06.2001, p. 4635-4642.

Research output: Contribution to journalArticle

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