Chemistry–A European Journal

Sulfinylnitriles: Sulfinyl–Metal Exchange–Alkylation Strategies

D Nath, FF Fleming

Index: Nath, Dinesh; Fleming, Fraser F. Chemistry - A European Journal, 2013 , vol. 19, # 6 p. 2023 - 2029

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Citation Number: 7

Abstract

Abstract Adding organolithiums, Grignard reagents, or zincates to sulfinylnitriles triggers a facile sulfinyl–metal exchange to afford N-or C-metalated nitriles. Sulfinyl–magnesium exchange–alkylations efficiently install quaternary and tertiary centers, even in the case of tertiary sulfinylnitriles that contain a highly acidic methine proton. α-Sulfinylalkenenitriles afford moderately nucleophilic magnesiated nitriles, and the reactivity can be dramatically ...