Electrochemical C(sp3)-H functionalization of ethers via hydrogen-atom transfer by means of cathodic reduction

Chem Commun (Camb). 2023 Feb 28;59(18):2664-2667. doi: 10.1039/d2cc06999g.

Abstract

The chemo- and stereoselective electrochemical allylation/alkylation of ethers is presented via a C(sp3)-H activation event. The electrosynthetic protocol enables the realization of a large library of functionalized ethers (35 examples) in high yields (up to 84%) via cathodic activation of a new type of redox-active carbonate (RAC), capable of triggering HAT (Hydrogen-Atom-Transfer) events through the generation of electrophilic oxy radicals. The process displayed high functional group tolerance and mild reaction conditions. A mechanistic elucidation via voltammetric analysis completes the study.