Synthesis of Catechols from Phenols via Pd-Catalyzed Silanol-Directed C-H Oxygenation

A silanol-directed, Pd-catalyzed C-H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon protected catechol, A routine desilylation of the silacyle With TBAF uncovers the catechol product: