Novel Carbon-Carbon Bond-Forming Reactions Using Carbocations Produced from Substituted Propargyl Silyl Ethers by the Action of TMSOTf

T Ishikawa, M Okano, T Aikawa…

Index: Ishikawa; Okano; Aikawa; Saito Journal of Organic Chemistry, 2001 , vol. 66, # 13 p. 4635 - 4642

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Citation Number: 61

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 ...