Many palladium(II)-catalyzed reactions for selective oxidation of organic molecules have been developed; however, these reactions often exhibit poor catalytic performance, especially when applied to C–H oxidation. These reactions commonly feature high Pd loading (e.g., 10 mol%) and/or require (super)stoichiometric quantities of undesirable oxidants, such as benzoquinone and silver(I) salts. We have previously noted that Pd-catalyzed oxidation reactions that generate products via beta-hydride elimination steps tend to exhibit higher Pd turnover numbers and better peformance with O2 than reactions that generate products via reductive elimination (Acc. Chem. Res. 2012, 45, 851-863). This talk will address these issues and highlight our recent study of Pd-catalyzed C–H arylation reactions. Quinone co-catalysts have both beneficial and deleterious impact on these reactions, and mechanistic insights into these effects enabled some of the best catalytic performance ever observed for Pd-catalyzed C–H oxidation reactions.

Accessing "good catalysis" in palladium-catalyzed C–H aerobic oxidation reactions

ACS Spring Meeting 2021

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