Visible Light-Catalyzed Benzylic C-H Bond Chlorination by a Combination of Organic Dye (Acr⁺-Mes) and N-Chlorosuccinimide

Ming Xiang, Chao Zhou, Xiu-Long Yang, Bin Chen, Chen-Ho Tung and Li-Zhu Wu*

*University of Chinese Academy of Sciences, The Chinese Academy of Sciences, Beijing 100190, P. R. China, Email: lzwumail.ipc.ac.cn

M. Xiang, C. Zhou, X.-L. Yang, B. Chen, C.-H. Tung, L.-Z. Wu, J. Org. Chem., 2020, 85, 9080-9087.

DOI: 10.1021/acs.joc.0c01000

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Abstract

The combination of N-chlorosuccinimide as safe chlorine source with Acr⁺-Mes as the photocatalyst achieves a benzylic C-H bond chlorination under visible light irradiation. This mild and scalable chlorination method worked effectively for electron-deficient substrates. Furthermore, benzylic chlorides could be converted to benzylic ethers smoothly in one-pot by adding sodium methoxide.

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Key Words

benzylic chlorination, NCS, photochemistry

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ID: J42-Y2020