Thermodynamic-Kinetic Comparison of Palladium(II)-Mediated Alcohol and Hydroquinone Oxidation.

ABSTRACT: Palladium(II) catalysts promote oxidative dehydrogenation and dehydrogenative coupling of many organic molecules. Oxidations of alcohols to aldehydes or ketones are prominent examples. Hydroquinone (H₂Q) oxidation to benzoquinone (BQ) is conceptually related to alcohol oxidation, but it is significantly more challenging thermodynamically. The BQ/H₂Q redox potential is sufficiently high that BQ is often used as an oxidant in Pd-catalyzed oxidation reactions. A recent report (J. Am Chem. Soc. 2020, 142, 19678-19688) showed that certain ancillary ligands can raise the Pd^II/0 redox potential sufficiently to reverse this reactivity, enabling (L)Pd^II(OAc)₂ to oxidize hydroquinone to benzoquinone. Here, we investigate the

SUBMITTER: Bruns DL 

PROVIDER: S-EPMC9916251 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature