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Electrochemical Decarboxylative Sulfonylation of Cinnamic Acids with Aromatic Sulfonylhydrazides to Vinyl Sulfones

Yu Zhao, Yin-Long Lai, Ke-Si Du, Dian-Zhao Lin and Jing-Mei Huang*

*Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510640, China, Email: chehjmscut.edu.cn

Y. Zhao, Y.-L. Lai, K.-S. Du, D.-Z. Lin, J.-M. Huang, J. Org. Chem., 2017, 82, 9655-9661.

DOI: 10.1021/acs.joc.7b01741 (free Supporting Information)



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Abstract

An electrochemical oxidative N-S bond cleavage of aromatic sulfonylhydrazides, followed by cross-coupling reaction with cinnamic acids enable a stereoselective synthesis of (E)-vinyl sulfones in good yields with wide substrate scope under metal-free and halogen-free conditions.

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proposed mechanism



Key Words

vinyl sulfones, electrochemistry


ID: J42-Y2017