Photoinduced Carbon Tetrabromide Initiated Aerobic Oxidation of Substituted Toluenes to Carboxylic Acids

Kun Zheng, Xiaoyu Yan, Guofu Zhang, Xinhuan Yan, Xiaoqing Li*, Xiangsheng Xu*

*College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China, Email: xqlizjut.edu.cn, futurezjut.edu.cn

K. Zheng, X. Yan, G. Zhang, X. Yan, X. Li, X. Xu, Synlett, 2020, 31, 272-274.

DOI: 10.1055/s-0039-1691534

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Abstract

The use of CBr₄ as initiator enables a mild and metal-free aerobic oxidation of substituted toluenes to carboxylic acids under irradiation from a 400 nm blue light-emitting diode.

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Note

The reaction is inherently explosive in nature because significant concentrations of peroxide and hydroperoxide intermediates are generated. Approriate precautions should be adopted. The reaction should not be scaled up.

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Key Words

metal-free synthesis, photochemistry, photooxidation, toluenes, benzoic acids, oxygen

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ID: J72-Y2020