Photoredox-Catalyzed Decarboxylative Elimination via Halogen Atom Transfer

Enamides and enecarbamates offer an excellent balance between stability and reactivity. Decarboxylation of widely available amino acids offers a green and efficient alternative to accessing these reagents. The present study describes a photocatalytic approach for the direct decarboxylative synthesis of enamides via sequential radical decarboxylation and putative halogen-atom transfer (XAT). This operationally simple, economical protocol is scalable and allows for mild reaction conditions and short reaction times. In addition, it obviates the need for transition metals and preactivation of carboxylic acids.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-04-08
DOI
https://doi.org/10.1021/acs.joc.5c00237
Citations
5
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
4.68

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article

Photoredox-Catalyzed Decarboxylative Elimination via Halogen Atom Transfer

Deshkanwar Singh Brar, Jon A. Tunge, Roberto Aponte
5 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
4.68
article

Photoredox-Catalyzed Decarboxylative Elimination via Halogen Atom Transfer

Deshkanwar Singh Brar, Jon A. Tunge, Roberto Aponte
article en
5 citations

Abstract

Enamides and enecarbamates offer an excellent balance between stability and reactivity. Decarboxylation of widely available amino acids offers a green and efficient alternative to accessing these reagents. The present study describes a photocatalytic approach for the direct decarboxylative synthesis of enamides via sequential radical decarboxylation and putative halogen-atom transfer (XAT). This operationally simple, economical protocol is scalable and allows for mild reaction conditions and short reaction times. In addition, it obviates the need for transition metals and preactivation of carboxylic acids.

The Journal of Organic ChemistryVol. 90(15)
University of Kansas (US)
National Science Foundation, Division of Chemistry
Openalex Percentile: Top 6%
Radical Photochemical Reactions
4.68
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