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