Photoredox-Catalyzed Cascade Radical Cyclization of Ester Arylpropiolates with CF₃SO₂Cl To Construct 3-Trifluoromethyl Coumarin Derivatives

Long Chen, Lianlian Wu, Weijie Duan, Tao Wang*, Letian Li, Keke Zhang, Jingmei Zhu, Zhi Peng, Fei Xiong*

*Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi , Email: wangtaojxnu.edu.cn, xiongfeijxnu.edu.cn

L. Chen. L. Wu, W. Duan, T. Wang, L. Li, K. Zhang, J. Zhu, Z. Peng, F. Xiong, J. Org. Chem., 2018, 83, 8607-8614.

DOI: 10.1021/acs.joc.8b00581

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Abstract

The use of CF₃SO₂Cl as the trifluoromethyl radical source enables a highly efficient synthesis of 3-trifluoromethyl coumarins in very good yields from ester 3-arylpropiolates under visible light irradiation. The reaction incorporates a cascade cyclization/dearomatization/ester migration/oxidization/rearomatization process.

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Key Words

coumarins, photochemistry

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ID: J42-Y2018