Steric Control of Site Selectivity in the Pd-Catalyzed C–H Acetoxylation of Simple Arenes

This report describes the use of an oxidant and a ligand to control site selectivity in the Pd(OAc)2-catalyzed C-H acetoxylation of simple arenes. The use of MesI(OAc)2 as the terminal oxidant in combination with acridine as the ligand results in primarily sterically controlled selectivity. In contrast, with Pd(OAc)2 as the catalyst and PhI(OAc)2 as the oxidant, electronic effects dominate the selectivity of arene C-H acetoxylation.