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Sulfinylnitriles: Sulfinyl-Metal Exchange-Alkylation Strategies
Journal article   Peer reviewed

Sulfinylnitriles: Sulfinyl-Metal Exchange-Alkylation Strategies

Dinesh Nath and Fraser F. Fleming
Chemistry : a European journal, v 19(6), pp 2023-2029
04 Feb 2013
PMID: 23280544

Abstract

Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology
Adding organolithiums, Grignard reagents, or zincates to sulfinylnitriles triggers a facile sulfinylmetal exchange to afford N- or C-metalated nitriles. Sulfinylmagnesium exchangealkylations efficiently install quaternary and tertiary centers, even in the case of tertiary sulfinylnitriles that contain a highly acidic methine proton. -Sulfinylalkenenitriles afford moderately nucleophilic magnesiated nitriles, and the reactivity can be dramatically increased by conversion to the corresponding magnesiates. The sulfinyl-metal exchange is extremely fast, proceeds efficiently with quaternary, tertiary, and vinylic -sulfinylnitriles, and exhibits an exceptional functional group tolerance in nitrile alkylations.

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