Electrochemical oxidative thiocyanation and amination of enaminones towards the synthesis of multi-substituted alkenes

Fangling Lu; Kan Zhang; Yanxiu Yao; Ying Yin; Jiafu Chen; Xinwei Zhang; Yin Wang; Lijun Lu; Ziwei Gao; Aiwen Lei

doi:10.1039/D0GC03590D

Electrochemical oxidative thiocyanation and amination of enaminones towards the synthesis of multi-substituted alkenes†

Fangling Lu,‡^a Kan Zhang,‡^a Yanxiu Yao,^a Ying Yin,^b Jiafu Chen,^b Xinwei Zhang,^b Yin Wang,^b Lijun Lu,*^c Ziwei Gao

*^a and Aiwen Lei

*^bc

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* Corresponding authors

^a College of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, P.R. China
E-mail: zwgao@snnu.edu.cn

^b National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. China

^c The Institute for Advanced Studies (IAS), College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. China
E-mail: ljlu@whu.edu.cn, aiwenlei@whu.edu.cn

Abstract

A highly stereoselective synthesis of thiocyanated enaminones was achieved by an electrochemical process, which involved C–H bond thiocyanation and vinyl C–N bond transamination. Various aryl enaminones were compatible, generating the desired thiocyanated enaminones in up to 87% yields. This transformation proceeded smoothly without an external oxidant, a supporting electrolyte and a transition-metal catalyst. Gram-scale synthesis showed the potential of this protocol for practical application.

Green Chemistry

Electrochemical oxidative thiocyanation and amination of enaminones towards the synthesis of multi-substituted alkenes†

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