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.