Metal-free electrochemical dihydroxylation of unactivated alkenes

Min Liu; Tian Feng; Yanwei Wang; Guangsheng Kou; Qiuyan Wang; Qian Wang; Youai Qiu

doi:10.1038/s41467-023-42106-8

Metal-free electrochemical dihydroxylation of unactivated alkenes

Nat Commun. 2023 Oct 13;14(1):6467. doi: 10.1038/s41467-023-42106-8.

Authors

Min Liu¹, Tian Feng¹, Yanwei Wang¹, Guangsheng Kou¹, Qiuyan Wang², Qian Wang¹, Youai Qiu³

Affiliations

¹ State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, China.
² State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, China. qywang@nankai.edu.cn.
³ State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, China. qiuyouai@nankai.edu.cn.

Abstract

Herein, a metal-free electrochemical dihydroxylation of unactivated alkenes is described. The transformation proceeds smoothly under mild conditions with a broad range of unactivated alkenes, providing valuable and versatile dihydroxylated products in moderate to good yields without the addition of costly transition metals and stoichiometric amounts of chemical oxidants. Moreover, this method can be applied to a range of natural products and pharmaceutical derivatives, further demonstrating its synthetic utility. Mechanistic studies have revealed that iodohydrin and epoxide intermediate are formed during the reaction process.