Electrocatalytic C-H/N-H Coupling of 2'-Aminoacetophenones for the Synthesis of Isatins

Peng Qian, Ji-Hu Su, Yukang Wang, Meixiang Bi, Zhenggen Zha* and Zhiyong Wang*

*Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China, Email: zgzhaustc.edu.cn, zwang3ustc.edu.cn

P. Qian, J.-H. Su, Y. Wang, M. Bi, Z. Zha, Z. Wang, J. Org. Chem., 2017, 82, 6434-6440.

DOI: 10.1021/acs.joc.7b00635

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Abstract

A simple electrochemical oxidation of 2'-aminoacetophenones in the presence of n-Bu₄NI provides various isatins with moderate to good yields via C(sp³)-H oxidation followed by intramolecular C-N bond formation. A radical-based pathway is proposed.

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proposed mechanism

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Key Words

isatins, electrochemistry, oxygen

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ID: J42-Y2017