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

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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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-05-03
DOI
https://doi.org/10.1021/acs.joc.5c00595
Citations
7
Primary Topic
Synthesis and Catalytic Reactions
Type
article
Field-Weighted Citation Impact
6.55
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article

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

Elisabeth Bouwman, Jeroen D. C. Codée, Dennis Dam, Joeri Schoenmakers
7 citations
The Journal of Organic Chemistry
Synthesis and Catalytic Reactions
6.55
article

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

Elisabeth Bouwman, Jeroen D. C. Codée, Dennis Dam, Joeri Schoenmakers
article en
7 citations

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.

The Journal of Organic ChemistryVol. 90(19)
Leiden University (NL)
Clean water and sanitation
Openalex Percentile: Top 3%
Synthesis and Catalytic Reactions
6.55
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