Decarboxylative (Thio)esterification of α-Keto Acids via Carbonyl-Photoredox/Copper Dual Catalysis

An efficient visible-light-induced copper-catalyzed decarboxylative (thio)esterification of α-keto acids with (thio)phenols has been developed using 2-chloro-thioxanthen-9-one as the photocatalyst and dimethyl sulfoxide (DMSO) as the terminal oxidant and solvent, enabling the efficient synthesis of aryl (thio)benzoates in moderate to excellent yields (66 examples). This operationally simple protocol exhibits excellent tolerance toward various functional groups, has been applied to the synthesis of pharmaceutical/natural product derivatives, and proceeds efficiently on a gram scale.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-01-30
DOI
https://doi.org/10.1021/acs.joc.5c03066
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Decarboxylative (Thio)esterification of α-Keto Acids via Carbonyl-Photoredox/Copper Dual Catalysis

David James Young, Yanqing Wang, Hong-Xi Li, Da-Liang Zhu et al.
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
article

Decarboxylative (Thio)esterification of α-Keto Acids via Carbonyl-Photoredox/Copper Dual Catalysis

David James Young, Yanqing Wang, Hong-Xi Li, Da-Liang Zhu, Jie Li, Chang Cheng
article en

Abstract

An efficient visible-light-induced copper-catalyzed decarboxylative (thio)esterification of α-keto acids with (thio)phenols has been developed using 2-chloro-thioxanthen-9-one as the photocatalyst and dimethyl sulfoxide (DMSO) as the terminal oxidant and solvent, enabling the efficient synthesis of aryl (thio)benzoates in moderate to excellent yields (66 examples). This operationally simple protocol exhibits excellent tolerance toward various functional groups, has been applied to the synthesis of pharmaceutical/natural product derivatives, and proceeds efficiently on a gram scale.

The Journal of Organic ChemistryVol. 91(6)
Integrated Optoelectronics (Norway) (NO), Analysis and Testing Centre (CN), Yancheng Teachers University (CN), Minnan University of Science and Technology (CN), University of Glasgow (GB)
Openalex Percentile: Top 72%
Sulfur-Based Synthesis Techniques
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