Synthesis of unsymmetrical o-biphenols and o-binaphthols via silicon-tethered Pd-catalyzed C-H arylation

Chunhui Huang, Vladimir Gevorgyan

Research output: Contribution to journalArticle

34 Scopus citations

Abstract

A mild, practical, and efficient method for the synthesis of unsymmetrical o-biphenols (including o-phenol-naphthols and o-binaphthols) has been developed. Unsymmetrical bis-aryloxy silanes, which were readily prepared in a semi-one-pot fashion, underwent the Pd-catalyzed intramolecular arylation followed by a routine TBAF desilylation step to furnish valuable unsymmetrical biphenols without necessity of isolation of seven-membered intermediates. The excellent functional group tolerance allows for synthesis of a variety of functionalized o-biphenols and o-binaphthols from easily available staring materials.

Original languageEnglish (US)
Pages (from-to)2442-2445
Number of pages4
JournalOrganic Letters
Volume12
Issue number10
DOIs
StatePublished - May 21 2010
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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