Electrosynthesis of 2-Substituted Benzoxazoles via Intramolecular Shono-Type Oxidative Coupling of Glycine Derivatives

Lei Liu, Zhenhui Xu, Tao Liu, Chao Xu, Wangqin Zhang, Xiangqi Hua, Fei Ling* and Weihui Zhong*

*College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, People’s Republic of China, Email: lingfeizjut.edu.cn, weihuizhongzjut.edu.cn

L. Liu, Z. Xu, T. Liu, C. Xu, W. Zhang, X. Hua, F. Ling, W. Zhong, J. Org. Chem., 2022, 87, 11379-11386.

DOI: 10.1021/acs.joc.2c00856

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Abstract

An atom-economical and eco-friendly electrochemical oxidation/cyclization of glycine derivatives through intramolecular Shono-type oxidative coupling provides a variety of 2-substituted benzoxazoles in good yields. This oxidative cyclization proceeded in transition metal- and oxidant-free conditions and generated H₂ as only byproduct.

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proposed mechanisms

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Key Words

benzoxazoles, electrochemistry

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ID: J42-Y2022