Scalable, Electrochemical Oxidation of Unactivated C-H Bonds

A practical electrochemical oxidation of unactivated C-H bonds is presented. This reaction utilizes a simple redox mediator, quinuclidine, with inexpensive carbon and nickel electrodes to selectively functionalize deep-seated methylene and methine moieties. The process exhibits a broad scope and good functional group compatibility. The scalability, as illustrated by a 50 g scale oxidation Of sclareolide, bodes well for immediate and widespread adoption.