Synthesis of Catechols from Phenols Via Pd-catalyzed Silanol-directed C-H Oxygenation

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2011 Oct 18

PMID 21999512

Citations 28

Authors

Chunhui Huang

Nugzar Ghavtadze

Buddhadeb Chattopadhyay

Vladimir Gevorgyan

Affiliations

Soon will be listed here.

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.

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