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 journalArticle

109 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)17630-17633
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number44
DOIs
StatePublished - Nov 9 2011
Externally publishedYes

Fingerprint

Catechols
Oxygenation
Phenols
Electrons
Cyclization
Silicon
Acids
silanol
catechol

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Synthesis of catechols from phenols via Pd-catalyzed silanol-directed C-H oxygenation. / Huang, Chunhui; Ghavtadze, Nugzar; Chattopadhyay, Buddhadeb; Gevorgyan, Vladimir.

In: Journal of the American Chemical Society, Vol. 133, No. 44, 09.11.2011, p. 17630-17633.

Research output: Contribution to journalArticle

Huang, Chunhui ; Ghavtadze, Nugzar ; Chattopadhyay, Buddhadeb ; Gevorgyan, Vladimir. / Synthesis of catechols from phenols via Pd-catalyzed silanol-directed C-H oxygenation. In: Journal of the American Chemical Society. 2011 ; Vol. 133, No. 44. pp. 17630-17633.
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