Copper-catalyzed selective oxidation of hydrazones through C(sp3)–H functionalization

Jiabin Shen; Xiaoying Jiang; Haifeng Wu; Jun Xu; Qing Zhu; Pengfei Zhang

doi:10.1039/D1OB01563J

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Copper-catalyzed selective oxidation of hydrazones through C(sp³)–H functionalization†

Jiabin Shen,^ab Xiaoying Jiang,^bc Haifeng Wu,^ab Jun Xu,^b Qing Zhu

*^a and Pengfei Zhang

*^b

Author affiliations

* Corresponding authors

^a Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China
E-mail: zhuq@zjut.edu.cn

^b College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, Zhejiang, People's Republic of China
E-mail: pfzhang@hznu.edu.cn

^c College of Chemistry and Chemical Engineering, Central south University, Changsha, P.R. China

Abstract

A simple and mild protocol for copper-catalyzed oxidation of hydrazones at the α-position has been reported. Various substrates are compatible, providing the corresponding products in moderate to good yields. This strategy provides an efficient and convenient solution for the synthesis of carbonyl hydrazone. A free radical pathway mechanism is suggested for the transformation.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D1OB01563J
Article type: Communication
Submitted: 09 Aug 2021
Accepted: 26 Sep 2021
First published: 27 Sep 2021

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Org. Biomol. Chem., 2021,19, 8917-8923

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Copper-catalyzed selective oxidation of hydrazones through C(sp³)–H functionalization

J. Shen, X. Jiang, H. Wu, J. Xu, Q. Zhu and P. Zhang, Org. Biomol. Chem., 2021, 19, 8917 DOI: 10.1039/D1OB01563J

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Organic & Biomolecular Chemistry