Copper-catalyzed direct thiolation of pentafluorobenzene with diaryl disulfides or aryl thiols by C-H and C-F bond activation

摘要

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 °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 _2O 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. The Cu-catalyzed cross-coupling of diaryl disulfides/thiols with pentafluorobenzene in the presence of CuBr and tBuOLi or tBuOK in DMSO at 60 °C under an O _2 atmosphere was investigated. The corresponding bisarylthiolation products wereobtained by C-H bond and C-F bond activation. When 1,10-phenanthroline·H _2O and DDQ were added to the above system, monoarylthiolation products could be isolated.