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

A Cu-catalyzed cross-coupling reaction of diaryl disulfides or aryl thiols with pentafluorobenzene using CuBr as the catalyst, tBuOLi or tBuOK as the base in DMSO at 60 degrees C under an O2 atmosphere was investigated. The corresponding bisarylthiolation products were obtained in moderate to good yields by CH bond and CF bond activation. When 1,10-phenanthroline center dot H2O 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 throughCH bond and CF bond activation.