Scalable, transition-metal-free direct oxime o-arylation: Rapid access to o-arylhydroxylamines and substituted benzo[b]furans

Hongyin Gao, Qing Long Xu, Craig Keene, László Kürti

Research output: Contribution to journalArticle

35 Scopus citations

Abstract

O-Aryloximes, generated from readily available and inexpensive oximes through transition-metal-free O-arylation, can either be hydrolyzed to O-arylhydroxylamines or conveniently converted to structurally diverse benzo[b]furans through an environmentally benign, one-pot [3,3]-sigmatropic rearrangement/cyclization sequence. A scalable, transition-metal-free (TM-free) direct O-arylation of ketone oximes with a wide range of diaryliodonium salts has been developed. More than two dozen O-arylated oximes have been prepared in good to excellent yields at ambient temperature and were converted to the corresponding substituted benzo[b]furans through a [3,3]-sigmatropic rearrangement/cyclization sequence. Overall, this operationally simple, environmentally benign, and protecting-group-free approach, including a one-pot variant, allows rapid and convenient synthetic access to substituted benzo[b]furans (see scheme).

Original languageEnglish (US)
Pages (from-to)8883-8887
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number29
DOIs
StatePublished - Jul 14 2014

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Keywords

  • O-arylation
  • benzofurans
  • cyclization
  • diaryliodonium salts
  • oximes
  • sigmatropic rearrangement
  • transition-metal free

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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