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 journalArticlepeer-review

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

ASJC Scopus subject areas

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

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