title: Rhodium-catalyzed synthesis of diaryl sulfides using aryl fluorides and sulfur/organopolysulfides.
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.
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai, 980-8578, Japan. arisawa@m.tohoku.ac.jp
authors.forename: Mieko
authors.initials: M
authors.lastname: Arisawa
authors.forename: Takuya
authors.initials: T
authors.lastname: Ichikawa
authors.forename: Masahiko
authors.initials: M
authors.lastname: Yamaguchi
mesh_terms: D002384:Catalysis; D005459:Fluorides / Q000737:chemistry*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry; D013455:Sulfur / Q000737:chemistry*
chemical_list: D013440:Sulfides; D013455:Sulfur; D012238:Rhodium; D005459:Fluorides