Discovery of practical production processes for arylsulfur pentafluorides and their higher homologues, bis- and tris(sulfur pentafluorides): Beginning of a new era of “super-trifluoromethyl” arene chemistry and its industry

• Teruo Umemoto,
• Lloyd M. Garrick and
• Norimichi Saito

Beilstein J. Org. Chem. 2012, 8, 461–471, doi:10.3762/bjoc.8.53

• attracted considerable interest in many areas such as medicines, agrochemicals, and other new materials, since the highly stable SF5 group is considered a “super-trifluoromethyl group” due to its significantly higher electronegativity and lipophilicity. This article describes the first practical method for

• economical production of various arylsulfur pentafluorides and their higher homologues, which could then open up a new era of “super-trifluoromethyl” arene chemistry and its applications in many areas. Keywords: arylsulfur chlorotetrafluoride; arylsulfur pentafluoride; pentafluorosulfanyl; sulfur

• pentafluoride; super-trifluoromethyl; Introduction Pentafluorosulfanyl (SF5) is considered a “super-trifluoromethyl group” as SF5 has the peculiarity of fluorine beyond a trifluoromethyl (CF3) group [1]. Arylsulfur pentafluorides (ArSF5) are very thermally and chemically stable [2]. Pioneering work by Sheppard