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

C Huang, N Ghavtadze, B Chattopadhyay…

Index: Huang, Chunhui; Ghavtadze, Nugzar; Chattopadhyay, Buddhadeb; Gevorgyan, Vladimir Journal of the American Chemical Society, 2011 , vol. 133, # 44 p. 17630 - 17633

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Citation Number: 80

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 ...