Rhodium-catalyzed transformation of heteroaryl aryl ethers into heteroaryl fluorides

Mieko Arisawa, Saori Tanii, Takeru Tazawa, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

A rhodium complex catalyzed the conversion of the C-O bond of heteroaryl aryl ethers to the C-F bond. The reaction of (4-chlorophenylthio)pentafluorobenzene with heteroaryl aryl ethers provided heteroaryl fluorides and heteroaryl (4-chlorophenylthio)tetrafluorophenyl ethers; this involved the cleavage of a single heteroaryl C-O bond under equilibrium conditions. The reaction of heteroaryl aryl ethers with 2-fluorobenzothiazole in which two heteroaryl and aryl C-O bonds were cleaved provided heteroaryl fluorides and aryl fluorides. The reactions were applicable to five-membered and six-membered heteroaryl aryl ethers and also to diaryl ethers possessing one or two electron-withdrawing groups.

Original languageEnglish
Pages (from-to)11390-11393
Number of pages4
JournalChemical Communications
Volume52
Issue number76
DOIs
Publication statusPublished - 2016

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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