Convenient Access to meta-Substituted Phenols by Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling and Oxidation.

Abstract

We report a new approach to the synthesis of meta-substituted phenols in which a single palladium catalyst accomplishes a Suzuki-Miyaura cross-coupling between a β-chlorocyclohexenone and an arylboronic acid, and oxidation of the resulting cyclohexenone to the corresponding phenol upon introduction of a terminal oxidant and electron transfer mediator. Notably, this method also allows ready access to ortho, meta-disubstituted phenols, sterically congested biaryl phenols, and more highly substituted phenols.