Oxidative cross-coupling of substituted phenols with unactivated aromatics

Nagnath Yadav More, Masilamani Jeganmohan

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

A regioselective C–H arylation of substituted phenols or naphthols with substituted aromatics in the presence of K2S2O8 and Bu4N+·HSO4 in CF3COOH at ambient temperature providing unsymmetrical biaryls is described. The cross-coupling reaction is compatible with various substituted phenols and aromatics. Based on oxidation potential studies, it was observed that phenols with oxidation potentials up to 0.68 V and naphthols up to 0.88 V were compatible with the reaction. The cross-coupling reaction proceeds through the reaction of K2S2O8 with substituted phenol, providing a cationic phenol radical intermediate that was further converted into the phenoxy radical intermediate by the dissociation of H+. Subsequent radical-anion coupling of the phenoxy radical intermediate with a substituted aromatic affords the cross-coupling product. The formation of a cationic phenol radical intermediate and phenoxy radical intermediate were confirmed by UV/Vis and EPR studies.

Original languageEnglish
Pages (from-to)4305-4312
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number29
DOIs
StatePublished - 10 Aug 2017
Externally publishedYes

Keywords

  • Biaryls
  • Cross-coupling
  • Oxidative coupling
  • Phenols
  • Radical reactions
  • Regioselectivity

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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