Rhodium-catalyzed synthesis of diaryl sulfides using aryl fluorides and sulfur/organopolysulfides

Mieko Arisawa, Takuya Ichikawa, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

46 Citations (Scopus)

Abstract

Substituted pentafluorobenzenes react with sulfur to give bis(4-substituted 2,3,5,6-tetrafluorophenyl) sulfides in the presence of RhH(PPh 3)4, 1,2-bis(diphenylphosphino)benzene (dppBz), and tributylsilane. The reaction proceeds efficiently between room temperature and 80 °C. A comparative study of the reactivities of an organic trisulfide and a tetrasulfide showed notable substrate specificity. Di-tert-butyl tetrasulfide reacted with reactive aryl monofluorides and substituted pentafluorobenzenes. Di-tert-butyl trisulfide reacted with aryl monofluorides. The reactivity was explained on the basis of the difference in S-S bond energy.

Original languageEnglish
Pages (from-to)5318-5321
Number of pages4
JournalOrganic letters
Volume14
Issue number20
DOIs
Publication statusPublished - 2012 Oct 19

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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