Copper-catalyzed aerobic photodecarboxylation of carboxylic acids to aldehydes and ketones

Base-metal-catalyzed decarboxylative transformations provide an economic pathway to the efficient functionalization of carboxylic acids. Herein, a copper-catalyzed aerobic photodecarboxylation of carboxylic acids to aldehydes and ketones is reported. The reaction operates through a ligand-to-metal charge transfer (LMCT) mechanism under light irradiation, with molecular oxygen serving as the oxidant. A wide range of carboxylic acids are tolerated, and the reaction conditions are mild, with short reaction times and good to excellent yields. Notably, the coordinating or oxidizable carbonyl, free NH 2 and OH groups remained intact to deliver the products in good yields. Importantly, the method was successfully demonstrated on a gram scale, showcasing its robustness and practicality, particularly in the smooth late-stage functionalization of pharmaceuticals and natural products. A visible-light-driven copper-catalyzed protocol for the aerobic decarboxylative transformation of carboxylic acids into structurally diverse aldehydes and ketones was reported. This photocatalytic system operates through a ligand-to-metal charge transfer (LMCT) activation mechanism, utilizing molecular oxygen as a green oxidant under mild reaction conditions.

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Publication Details

Journal
Green Synthesis and Catalysis
Published
2025-03-01
DOI
https://doi.org/10.1016/j.gresc.2025.03.006
Citations
2
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
Field-Weighted Citation Impact
1.87
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article

Copper-catalyzed aerobic photodecarboxylation of carboxylic acids to aldehydes and ketones

Yonghuan Wang, Biping Xu, Weiping Su, Xiaoming Jie et al.
2 citations
Green Synthesis and Catalysis
Oxidative Organic Chemistry Reactions
1.87
article

Copper-catalyzed aerobic photodecarboxylation of carboxylic acids to aldehydes and ketones

Yonghuan Wang, Biping Xu, Weiping Su, Xiaoming Jie, Xuan Xiao
article en
2 citations

Abstract

Base-metal-catalyzed decarboxylative transformations provide an economic pathway to the efficient functionalization of carboxylic acids. Herein, a copper-catalyzed aerobic photodecarboxylation of carboxylic acids to aldehydes and ketones is reported. The reaction operates through a ligand-to-metal charge transfer (LMCT) mechanism under light irradiation, with molecular oxygen serving as the oxidant. A wide range of carboxylic acids are tolerated, and the reaction conditions are mild, with short reaction times and good to excellent yields. Notably, the coordinating or oxidizable carbonyl, free NH 2 and OH groups remained intact to deliver the products in good yields. Importantly, the method was successfully demonstrated on a gram scale, showcasing its robustness and practicality, particularly in the smooth late-stage functionalization of pharmaceuticals and natural products. A visible-light-driven copper-catalyzed protocol for the aerobic decarboxylative transformation of carboxylic acids into structurally diverse aldehydes and ketones was reported. This photocatalytic system operates through a ligand-to-metal charge transfer (LMCT) activation mechanism, utilizing molecular oxygen as a green oxidant under mild reaction conditions.

Green Synthesis and Catalysis
Fujian Normal University (CN), ShanghaiTech University (CN), Fujian Institute of Research on the Structure of Matter (CN)
Clean water and sanitation
Openalex Percentile: Top 17%
Oxidative Organic Chemistry Reactions
1.87
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