Electrochemical Palladium-Catalyzed Oxidative Sonogashira Carbonylation of Arylhydrazines and Alkynes to Ynones

Yong Wu, Li Zeng, Haoran Li, Yue Cao, Jingcheng Hu, Minghao Xu, Renyi Shi*, Hong Yi* and Aiwen Lei*

*Xi'an Jiaotong University, Xi’an 710049; Wuhan University, Wuhan 430072, P. R. China, Email: renyi.shixjtu.edu.cn, yihong1024163.com, aiwenleiwhu.edu.cn

Y. Wu, L. Zeng, H. Li, Y. Cao, J. Hu, M. Xu, R. Shi, H. Yi, A. Lei, J. Am. Chem. Soc., 2021, 143, 12460-12466.

DOI: 10.1021/jacs.1c06036

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Abstract

An oxygen-free, electrochemical palladium-catalyzed oxidative carbonylation of arylhydrazines with alkynes avoids the explosion hazard of CO. This variant of a carbonylative Sonogashira reaction efficiently provides ynones from easily accessible arylhydrazines and alkynes under copper-free conditions.

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proposed mechanism

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Key Words

Sonogashira coupling, ynones, electrochemistry

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ID: J48-Y2021