Peroxide- and transition metal-free electrochemical synthesis of α,β-epoxy ketones

Mengxun Zhang; Tie Chen; Shisong Fang; Weihua Wu; Xin Wang; Haiqiang Wu; Yongai Xiong; Jun Song; Chenyang Li; Zhendan He; Chi-Sing Lee

doi:10.1039/D0OB02444A

Peroxide- and transition metal-free electrochemical synthesis of α,β-epoxy ketones†

Mengxun Zhang,^ab Tie Chen,^a Shisong Fang,^c Weihua Wu,^c Xin Wang,^c Haiqiang Wu,^a Yongai Xiong,^a Jun Song,

^b Chenyang Li,*^a Zhendan He*^ad and Chi-Sing Lee

*^e

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* Corresponding authors

^a Department of Pharmacy, School of Medicine, Health Science Center, Shenzhen University, Shenzhen 518060, China
E-mail: hezhendan@szu.edu.cn

^b College of physics and optoelectronic engineering, Shenzhen University, Shenzhen 518060, China

^c Shenzhen Center for Disease Control and Prevention, Shenzhen 518100, China

^d College of Pharmacy, Shenzhen Technology University, Shenzhen 518118, China

^e Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong SAR, China

Abstract

A novel electrochemical method for the synthesis of α,β-epoxy ketones is reported. With KI as the redox mediator, methyl ketones reacted with aldehydes under peroxide- and transition metal-free electrolytic conditions and afforded α,β-epoxy ketones in one pot (36 examples, 52–90% yield). This safe and environmental-friendly method has a broad substrate scope and can readily provide a variety of α,β-epoxy ketones in gram-scales for evaluation of their anti-cancer activities.

This article is part of the themed collections: Synthetic electrochemistry and Synthetic methodology in OBC

Organic & Biomolecular Chemistry

Peroxide- and transition metal-free electrochemical synthesis of α,β-epoxy ketones†

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Peroxide- and transition metal-free electrochemical synthesis of α,β-epoxy ketones

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