Palladium-Catalyzed C–H Bond Acetoxylation via Electrochemical Oxidation

Here we describe the development of a method for the Pd-catalyzed electrochemical acetoxylation of C–H bonds. The oxidation step of the catalytic cycle is probed through cyclic voltammetry and bulk electrolysis studies of a preformed palladacycle of 8-methylquinoline. A catalytic system for C–H acetoxylation is then developed and optimized with respect to the cell configuration, rate of oxidation, and chemistry at the counter electrode. This transformation is then applied to substrates containing various directing groups and to the acetoxylation of both C­(sp2)–H and C­(sp3)–H bonds.