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Synthesis of catechols from phenols via Pd-catalyzed silanol-directed C-H oxygenation.

ABSTRACT: 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.

SUBMITTER: Huang C 

PROVIDER: S-EPMC3250381 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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Synthesis of catechols from phenols via Pd-catalyzed silanol-directed C-H oxygenation.

Huang Chunhui C   Ghavtadze Nugzar N   Chattopadhyay Buddhadeb B   Gevorgyan Vladimir V  

Journal of the American Chemical Society 20111018 44

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. ...[more]

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