Electrochemical Deconstructive Functionalization of Cycloalkanols via Alkoxy Radicals Enabled by Proton-Coupled Electron Transfer

Herein, we report a new electrochemical method for alkoxy radical generation from alcohols using a proton-coupled electron transfer (PCET) approach, showcased via the deconstructive functionalization of cycloalkanols. The electrochemical method is applicable across a diverse array of substituted cycloalkanols, accessing a broad range of synthetically useful distally functionalized ketones. The orthogonal derivatization of the products has been demonstrated through chemoselective transformations, and the electrochemical process has been performed on a gram scale in continuous single-pass flow.

Automated summary

A new electrochemical method for the generation of alkoxy radicals from alcohols using proton-coupled electron transfer (PCET) approach has been reported. The method allows the functionalization of cycloalkanols and access to a broad range of synthetically useful distally functionalized ketones. The products can be orthogonally derivatized through chemoselective transformations. The electrochemical process has been successfully performed on a gram scale in continuous single-pass flow.