Pd-catalyzed aerobic oxidative C–H/C–H coupling of o-xylene is highly relevant to the commercial production of Upilex, a polyimide resin. In this work, the Stahl Group probed the role of a Cu-based cocatalyst in this reaction and showed that it does not play a redox role as is typically assumed for Pd-catalyzed oxidation reactions.
Mechanistic insights led to the identification of Fe(OTf)3 as an even more effective cocatalyst. The results of this study have broad implications for Pd-catalyzed C–H oxidation reactions that are now being investigated further in the Center.