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

Org Biomol Chem. 2021 Mar 21;19(11):2481-2486. doi: 10.1039/d0ob02444a. Epub 2021 Mar 3.

Authors

Mengxun Zhang¹, Tie Chen², Shisong Fang³, Weihua Wu³, Xin Wang³, Haiqiang Wu², Yongai Xiong², Jun Song⁴, Chenyang Li², Zhendan He⁵, Chi-Sing Lee⁶

Affiliations

¹ Department of Pharmacy, School of Medicine, Health Science Center, Shenzhen University, Shenzhen 518060, China. hezhendan@szu.edu.cn and College of physics and optoelectronic engineering, Shenzhen University, Shenzhen 518060, China.
² Department of Pharmacy, School of Medicine, Health Science Center, Shenzhen University, Shenzhen 518060, China. hezhendan@szu.edu.cn.
³ Shenzhen Center for Disease Control and Prevention, Shenzhen 518100, China.
⁴ College of physics and optoelectronic engineering, Shenzhen University, Shenzhen 518060, China.
⁵ Department of Pharmacy, School of Medicine, Health Science Center, Shenzhen University, Shenzhen 518060, China. hezhendan@szu.edu.cn and College of Pharmacy, Shenzhen Technology University, Shenzhen 518118, China.
⁶ Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong SAR, China.

PMID: 33656035
DOI: 10.1039/d0ob02444a

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.

Publication types

Research Support, Non-U.S. Gov't