Electrochemical heterodifunctionalization of α-CF3 alkenes to access α-trifluoromethyl-β-sulfonyl tertiary alcohols

Zhi-Peng Ye; Jie Gao; Xin-Yu Duan; Jian-Ping Guan; Fang Liu; Kai Chen; Jun-An Xiao; Hao-Yue Xiang; Hua Yang

doi:10.1039/D1CC03288G

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Electrochemical heterodifunctionalization of α-CF₃ alkenes to access α-trifluoromethyl-β-sulfonyl tertiary alcohols†

Zhi-Peng Ye,‡^a Jie Gao,‡^a Xin-Yu Duan,^a Jian-Ping Guan,^a Fang Liu,^a Kai Chen,

^a Jun-An Xiao,^b Hao-Yue Xiang

*^ac and Hua Yang

*^a

Author affiliations

* Corresponding authors

^a College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China
E-mail: hyangchem@csu.edu.cn, xianghaoyue@csu.edu.cn

^b College of Chemistry and Materials Science, Nanning Normal University, Nanning 530001, Guangxi, P. R. China

^c School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, Henan, P. R. China

Abstract

An unprecedented electrochemical heterodifunctionalization of α-CF₃ alkenes with benzenesulfonyl hydrazides was accomplished in this work, wherein a β-sulfonyl and a α-hydroxyl group were simultaneously incorporated across the olefinic double bond in a single operation. Consequently, a series of potentially medicinally valuable and densely functionalized α-trifluoromethyl-β-sulfonyl tertiary alcohols were assembled under mild conditions. Electrochemically-driven oxidative 1,2-difunctionlization of electron-deficient alkenes well obviates the need for oxidizing reagents, thus rendering this protocol more eco-friendly.

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Article information

DOI: https://doi.org/10.1039/D1CC03288G
Article type: Communication
Submitted: 21 Jun 2021
Accepted: 03 Aug 2021
First published: 03 Aug 2021

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Chem. Commun., 2021,57, 8969-8972

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Electrochemical heterodifunctionalization of α-CF₃ alkenes to access α-trifluoromethyl-β-sulfonyl tertiary alcohols

Z. Ye, J. Gao, X. Duan, J. Guan, F. Liu, K. Chen, J. Xiao, H. Xiang and H. Yang, Chem. Commun., 2021, 57, 8969 DOI: 10.1039/D1CC03288G

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Chemical Communications