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

Chunhui Huang; Nugzar Ghavtadze; Buddhadeb Chattopadhyay; Vladimir Gevorgyan

doi:10.1021/ja208572v

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

Chunhui Huang, Nugzar Ghavtadze, Buddhadeb Chattopadhyay, Vladimir Gevorgyan

Research output: Contribution to journal › Article › peer-review

139 Scopus citations

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.

Original language	English (US)
Pages (from-to)	17630-17633
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	44
DOIs	https://doi.org/10.1021/ja208572v
State	Published - Nov 9 2011
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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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.",

author = "Chunhui Huang and Nugzar Ghavtadze and Buddhadeb Chattopadhyay and Vladimir Gevorgyan",

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AU - Huang, Chunhui

AU - Ghavtadze, Nugzar

AU - Chattopadhyay, Buddhadeb

AU - Gevorgyan, Vladimir

PY - 2011/11/9

Y1 - 2011/11/9

N2 - 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.

AB - 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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IS - 44

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

Abstract

ASJC Scopus subject areas

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