Photocatalytic Nitrene Radical Anion Generation from Sulfonyl Azides for Intermolecular Aziridination of Unactivated Alkenes

Abstract

Aziridines are important structures in the contemporary organic synthesis and are used for several biological applications. Herein, we show that aziridines can be readily synthesized from alkenes by the reductive activation of sulfonyl azides, mediated by photoredox catalysis. Mechanistic studies indicate that the reaction proceeds through reactive nitrene radical anions instead of the more commonly encountered triplet nitrenes. A substrate scope is performed that showed good functional group compatibility.

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