Fluoroalkylated hypervalent sulfur fluorides: radical addition of arylchlorotetrafluoro-λ 6 -sulfanes to tetrafluoroethylene.

Fluorinated groups are essential hydrophobic groups in drug design. Combining a carbon-free tetrafluoro-λ 6 -sulfanyl (SF 4 ) group with a polyfluoroalkyl group (R F ) provides SF 4 R F groups, exhibiting high hydrophobicity with a short carbon chain. In this study, various aryltetrafluoro(polyfluoroalkyl)-λ 6 -sulfanes (ArSF 4 R F ) were synthesized through the radical addition of arylchlorotetrafluoro-λ 6 -sulfanes (ArSF 4 Cl) to tetrafluoroethylene. In addition, quantification of hydrophobic constants (π Ph ) indicated that the SF 4 group is considerably more hydrophobic than a difluoromethylene (CF 2 ) group. Further transformation reactions revealed the stabilities and reactivities of these novel fluorinated groups. The high hydrophobicity and synthetic utility of the SF 4 R F group lead to the potential applications of the SF 4 R F group in the pharmaceutical field.