Aliphatic Diazirines Synthesis Mediated by Mild N -Chlorosuccinimide Oxidation

Abstract Diazirines have been known for decades as effective photoreactive moieties, with valuable applications in chemoproteomics. In recent years, they have received increasing interest in synthetic chemistry. Until recently, their access required a multistep process, which may entail the use of metals and liquid ammonia. Herein, we present a one-pot approach based on the use of N-chlorosuccinimide as the sole oxidant source, providing a useful complement to existing methodologies, in particular, with electron-rich substrates.

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Journal
The Journal of Organic Chemistry
Published
2026-09-10
DOI
https://doi.org/10.1021/acs.joc.6c01373
Primary Topic
Synthesis and Catalytic Reactions
Type
article
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article

Aliphatic Diazirines Synthesis Mediated by Mild N -Chlorosuccinimide Oxidation

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The Journal of Organic Chemistry
Synthesis and Catalytic Reactions
article

Aliphatic Diazirines Synthesis Mediated by Mild N -Chlorosuccinimide Oxidation

Luca Marchisio, Chloé Rémondin, Cyrille Sabot, Victor Flon, Pierre‐Yves Renard, Isabelle Toubia, Sébastien Balieu
article en

Abstract

Abstract Diazirines have been known for decades as effective photoreactive moieties, with valuable applications in chemoproteomics. In recent years, they have received increasing interest in synthetic chemistry. Until recently, their access required a multistep process, which may entail the use of metals and liquid ammonia. Herein, we present a one-pot approach based on the use of N-chlorosuccinimide as the sole oxidant source, providing a useful complement to existing methodologies, in particular, with electron-rich substrates.

The Journal of Organic Chemistry
Centre National de la Recherche Scientifique (FR), Normandie Université (FR), Université de Rouen Normandie (FR), Institut National des Sciences Appliquées Rouen Normandie (FR)
Clean water and sanitation
Openalex Percentile: Top 20%
Synthesis and Catalytic Reactions
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