Iron-catalyzed selective oxidative arylation of phenols and biphenols

Vlada Vershinin, Alina Dyadyuk, Doron Pappo

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

The single-step synthesis of protected fucols and unnatural polyaryls by biomimetic oxidative cross-coupling between phenolic components and 1,3,5-trimethoxybenzene catalyzed by FeCl3 in fluorinated solvents is reported. The regioselectivity (ortho, meta or para) and the chemoselectivity (C[sbnd]C vs C[sbnd]O) in this highly efficient transformation are controlled by the phenolic ortho-groups of the growing phenolic oligomer. The reaction scope was examined by coupling biphenol derivatives with the nucleophilic arene to afford large polyaryl compounds that are not easily accessible by other means. The versatility of the catalytic system in designing polyaryl frameworks was demonstrated by performing a sequential oxidative phenol-phenol and phenol-arene coupling reaction that afforded a single polyaryl product in high efficiency.

Original languageEnglish
Pages (from-to)3660-3668
Number of pages9
JournalTetrahedron
Volume73
Issue number26
DOIs
StatePublished - 1 Jan 2017

Keywords

  • Consecutive reactions
  • Iron catalysis
  • Oxidative coupling
  • Phenols
  • Polyphenols

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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