Metal-free electrochemical dihydroxylation of unactivated alkenes

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. Methods to construct 1,2-diols have previously been developed, but often require the participation of a metal and are limited to activated alkenes. Here, the authors report a metal-free electrochemical dihydroxylation of unactivated alkenes providing valuable and versatile dihydroxylated products.