Umpolung Reactivity of Fluoroalkylselenotoluenesulfonates: Towards a Versatile Reagent

Fluoroalkylselenotoluenesulfonates, which have already been described as selenolating reagents in electrophilic and radical reactions, can also be reduced by an organic electron donor (namely tetrakis(dimethylamino) ethylene or TDAE) to generate the corresponding fluoroalkylselenolate anions. Thus, the in-situ-formed anions react with various alkyl halides in a metal-free nucleophilic substitution. Trifluoromethyl- and higher perfluroalkylselenolated compounds have been obtained in modest to good yields.