Electrochemical C(sp3)−H Functionalization Using Acetic Acid as a Hydrogen Atom Transfer Reagent

Abstract

In this study, we developed a novel electrochemical protocol that enables the functionalization of inherently inert C(sp3)−H bonds. In this protocol, one-electron oxidation of acetic acid was used to successfully generate methyl radical, which cleaves the benzylic C(sp3)−H bonds of the substrates via a hydrogen atom transfer (HAT) process, and further reaction with the formed species yields the targeted C(sp3)−H functionalized products. To the best of our knowledge, this is the first example of the use of acetic acid in a HAT process. Notably the reaction has environment-friendly and fine atom economy nature: the reaction is driven by the electrochemical conditions in the absence of expensive or hazardous reagents, producing only gaseous small molecules, hydrogen, carbon dioxide, and methane, as side products.