Novel carbon-carbon bond-forming reactions using carbocations produced from substituted propargyl silyl ethers by the action of TMSOTf.
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-(pi-donor)-substituted propargyl ethers by the action of trimethylsilyl trifluoromethanesulfonate in dichloromethane at -78 degrees 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.
Ishikawa
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Department of Bioscience and Biotechnology, Faculty of Engineering, Okayama University, Tsushima, Okayama, 700-8530, Japan.
Okano
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Aikawa
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Saito
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