Hydroxyl-directed C–C bond activation of benzophenones for the O-acylation of phenols

We report that 2-hydroxyl benzophenones can be converted to phenyl salicylate esters by loss of an aryl group and O-acylation of the phenols. Iridium, cyclooctadiene, and bulky monodentate phosphine ligands catalyze the ketone C–C bond activation and fragmentation. We identified common side products in this process, which include C-acylation of the phenol reactant or trapping on cyclooctadiene. Several of the processes reported here appear to be under equilibrium control. Overall, our report provides insight into the activation and functionalization of unstrained C–C bonds with group 9 catalysts.