Pentafluorosulfanylbenzene chemistry: Role of copper in the Sheppard reaction, direct fluorination of aromatic sulfenyl chlorides, and several potentially energetic SF5-benzenes

The Sheppard reaction most likely proceeds through the intermediacy of aryl thiolates whose formation from aromatic disulfides is catalyzed by coinage metal (M = Cu, Ag, and Au) surfaces. Aromatic sulfenyl chlorides were prepared from the chlorination of aromatic disulfides, and these substrates offer a new route to pentafluorosulfanybenzenes via their direct fluorination.