Transition-metal-free electrochemical oxidative C(sp2)–H trifluoromethylation of aryl aldehyde hydrazones

Yuan Shi; Kai Wang; Yuxin Ding; Yuanyuan Xie

doi:10.1039/D2OB01734B

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Transition-metal-free electrochemical oxidative C(sp²)–H trifluoromethylation of aryl aldehyde hydrazones†

Yuan Shi,^a Kai Wang,^b Yuxin Ding^a and Yuanyuan Xie

*^abc

Author affiliations

* Corresponding authors

^a College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, China
E-mail: xyycz@zjut.edu.cn

^b Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou, China

^c Key Laboratory of Pharmaceutical Engineering of Zhejiang Province, Hangzhou, China

Abstract

A simple protocol of metal-free C–H trifluoromethylation of hydrazones via electrolysis was developed. This environment-friendly transformation showed high efficiency, good tolerance, and scaled-up functionalization, providing the desired products in moderate to good yields. At the same time, a high yield can be obtained for the substrates either bearing an electron-donating group or an electron-withdrawing group by using different trifluoromethyl reagents. In addition, the radical mechanism was confirmed by the control experiment.

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Article information

DOI: https://doi.org/10.1039/D2OB01734B
Article type: Paper
Submitted: 22 Sep 2022
Accepted: 08 Nov 2022
First published: 15 Nov 2022

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Org. Biomol. Chem., 2022,20, 9362-9367

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Transition-metal-free electrochemical oxidative C(sp²)–H trifluoromethylation of aryl aldehyde hydrazones

Y. Shi, K. Wang, Y. Ding and Y. Xie, Org. Biomol. Chem., 2022, 20, 9362 DOI: 10.1039/D2OB01734B

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Organic & Biomolecular Chemistry