Modular Photochemical Approach to Access α-CF <sub>3</sub> -β-Aryl Carboxylic Acids via an Electron Donor–Acceptor Complex

α-CF 3 -β-aryl carboxylic acids are important precursors for emerging pharmaceuticals and bioactive compounds, but their utility is restricted by immature synthetic methodologies. However, the widespread application is limited by immature synthetic methods, such as the use of reactive substrates and expensive metal reagents and poor substrate compatibility. Herein, a visible light strategy is reported for the synthesis of α-CF 3 -β-aryl carboxylic acids via the arylation of 2-(trifluoromethyl)acrylic acid. A reaction mechanism involving electron donor–acceptor (EDA) complex formation between thianthrenium salts and diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (HE) to furnish the desired products was proposed. The reaction proceeds efficiently in the absence of any photocatalysts or transition metal catalysts, thereby holding promise for applications in pharmaceutical and fluorine chemistry.

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Publication Details

Journal
Organic Letters
Published
2026-06-17
DOI
https://doi.org/10.1021/acs.orglett.6c02056
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Modular Photochemical Approach to Access α-CF 3 -β-Aryl Carboxylic Acids via an Electron Donor–Acceptor Complex

Yiyong Huang, Zhi-Hao Yi, Zhang Zhang-de, Zhi‐Bing Dong et al.
Organic Letters
Fluorine in Organic Chemistry
article

Modular Photochemical Approach to Access α-CF 3 -β-Aryl Carboxylic Acids via an Electron Donor–Acceptor Complex

Yiyong Huang, Zhi-Hao Yi, Zhang Zhang-de, Zhi‐Bing Dong, Zhipeng Guan, Xinyu Lin, Xin Gao, Jun Dai, Zhan-Tu Zou
article en

Abstract

α-CF 3 -β-aryl carboxylic acids are important precursors for emerging pharmaceuticals and bioactive compounds, but their utility is restricted by immature synthetic methodologies. However, the widespread application is limited by immature synthetic methods, such as the use of reactive substrates and expensive metal reagents and poor substrate compatibility. Herein, a visible light strategy is reported for the synthesis of α-CF 3 -β-aryl carboxylic acids via the arylation of 2-(trifluoromethyl)acrylic acid. A reaction mechanism involving electron donor–acceptor (EDA) complex formation between thianthrenium salts and diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (HE) to furnish the desired products was proposed. The reaction proceeds efficiently in the absence of any photocatalysts or transition metal catalysts, thereby holding promise for applications in pharmaceutical and fluorine chemistry.

Organic Letters
China Three Gorges University (CN), Wuhan University of Technology (CN), Henan Normal University (CN), Wuhan Institute of Technology (CN)
Hubei Provincial Department of Education, National Natural Science Foundation of China, Natural Science Foundation of Hubei Province, Hubei Association for Science and Technology, Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology Department, Hubei Three Gorges Laboratory
Openalex Percentile: Top 9%
Fluorine in Organic Chemistry
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