Visible Light Mediated Chemoselective Hydroxylation of Benzylic Methylenes

Zhiyong Tan*, Tingting Chen, Jinbin Zhu, Wenjun Luo, Daohong Yu, Wei Guo*

*Key Laboratory of Organo-Pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, China, Email: 453759122qq.com, guoweigw126.com

Z. Tan, T. Chen, J. Zhu, W. Luo, D. Yu, W. Guo, J. Org. Chem., 2024, 89, 2656-2664.

DOI: 10.1021/acs.joc.3c02683

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Abstract

A metal-free photocatalytic selective hydroxylation of benzylic methylenes to secondary alcohols utilizes low-cost eosin Y as photocatalyst, O₂ as green oxidant, and inexpensive triethylamine as inhibitor for overoxidation. The mild reaction conditions enable the production of secondary benzylic alcohols in good yields.

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proposed mechanism

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Key Words

indolines, tetrahydroquinolines, oxygen, photochemistry

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ID: J42-Y2024