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

Abstract In honor of the awardee Dr. Teruo Umemoto and his significant advances in the preparation of pentafluorosulfanylbenzenes [1] , we will first overview our results aimed at understanding the importance of copper (and other coinage metals) in W.A. Sheppard's original synthesis of SF 5 -benzenes [2] as well as a new route to SF 5 -benzenes involving the direct fluorination of aromatic sulfenyl chlorides (Ar–S–Cl). Further nucleophilic substitution chemistry of the active halogen atom in 1-chloro-2,6-dinitrobenzene-4-pentafluorosulfanylbenzene will be presented, including chemistry aimed at potentially energetic materials such as an SF 5 -analog of picric acid.