Copper‐Catalyzed Enantioselective Decarboxylative Cyanation of Carboxylic Acids via Electrophotocatalysis

Carboxylic acids are important chemical feedstocks, and direct decarboxylative asymmetric transformation holds significant synthetic value. Herein, we report a copper‐catalyzed direct enantioselective decarboxylative cyanation of benzyl carboxylic acids under electrophotocatalytic conditions. Benzylic radicals are efficiently generated via ligand–to–metal charge transfer of copper(II) carboxylate species under irradiation of blue LEDs. Concurrently, the generation of copper(II) cyanide occurred simultaneously at the anode via electro‐oxidation, avoiding the use of the stoichiometric amount of chemical oxidants. Then the coupling of benzylic radical and chiral Cu(II) cyanide leads to enantioselective decarboxylative cyanation. This reaction features a broad substrate scope and excellent functional group tolerance, enabling the direct conversion of carboxylic acids into diverse chiral benzyl nitriles.

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Publication Details

Journal
ChemistryEurope
Published
2026-02-25
DOI
https://doi.org/10.1002/ceur.202500389
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00
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article

Copper‐Catalyzed Enantioselective Decarboxylative Cyanation of Carboxylic Acids via Electrophotocatalysis

Xueyao Zhao, Liu Guo-sheng, Wenzheng Fan, Pinhong Chen
ChemistryEurope
Radical Photochemical Reactions
article

Copper‐Catalyzed Enantioselective Decarboxylative Cyanation of Carboxylic Acids via Electrophotocatalysis

Xueyao Zhao, Liu Guo-sheng, Wenzheng Fan, Pinhong Chen
article en

Abstract

Carboxylic acids are important chemical feedstocks, and direct decarboxylative asymmetric transformation holds significant synthetic value. Herein, we report a copper‐catalyzed direct enantioselective decarboxylative cyanation of benzyl carboxylic acids under electrophotocatalytic conditions. Benzylic radicals are efficiently generated via ligand–to–metal charge transfer of copper(II) carboxylate species under irradiation of blue LEDs. Concurrently, the generation of copper(II) cyanide occurred simultaneously at the anode via electro‐oxidation, avoiding the use of the stoichiometric amount of chemical oxidants. Then the coupling of benzylic radical and chiral Cu(II) cyanide leads to enantioselective decarboxylative cyanation. This reaction features a broad substrate scope and excellent functional group tolerance, enabling the direct conversion of carboxylic acids into diverse chiral benzyl nitriles.

ChemistryEuropeVol. 4(3)
Shanghai Institute of Organic Chemistry (CN)
Openalex Percentile: Top 39%
Radical Photochemical Reactions
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