Copper‐Catalyzed Direct Thiolation of Pentafluorobenzene with Diaryl Disulfides or Aryl Thiols by C–H and C–F Bond Activation

Abstract

Abstract A Cu‐catalyzed cross‐coupling reaction of diaryl disulfides or aryl thiols with pentafluorobenzene using CuBr as the catalyst, t BuOLi or t BuOK as the base in DMSO at 60 °C under an O 2 atmosphere was investigated. The corresponding bisarylthiolation products were obtained in moderate to good yields by C–H bond and C–F bond activation. When 1,10‐phenanthroline · H 2 O and DDQ were added to the above system, monoarylthiolation products, with/without bisarylthiolation products, could be isolated in moderate yields. A plausible mechanism for these transformations was given. Thus, it represents a method for the synthesis of polyfluorinated diaryl sulfides and polyfluorinated triarylbisulfides throughC–H bond and C–F bond activation.