Phenylsulfanyltetrafluoroethanesulfonyl fluoride serves as a moderately reactive phenylsulfanyltetrafluoroethanesulfonylation reagent. A phenylsulfanyltetrafluoroethyl moiety incorporated in the substrate can be treated with tributyltin hydride and generate the corresponding fluoroalkyl radical which can add to neighbouring olefins, creating tetrafluorinated carbocycles. If the substrate lacks any olefins, it can be reduced to a tetrafluoroethyl group. Generally, fluoroalkylsulfonylation of the amine nitrogen greatly lowers the pKa value of the N-H and can be used to modulate the behaviour of the drug candidate or build additional molecular complexity around the highly acidic fluoroalkylsulfonamide nitrogen.
