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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2011-11, Vol.133 (44), p.17630-17633
Main Authors: Huang, Chunhui, Ghavtadze, Nugzar, Chattopadhyay, Buddhadeb, Gevorgyan, Vladimir
Format: Article
Language:English
Subjects:
Catalysis
Catechols - chemical synthesis
Catechols - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Oxygen - chemistry
Palladium - chemistry
Phenols - chemistry
Silanes - chemistry
Stereoisomerism
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja208572v