Nucleophilic fluoroalkylation of epoxides with fluorinated sulfones

The unprecedented nucleophilic fluoroalkylation of simple epoxides with fluorinated sulfones was achieved to give the beta-fluoroalkyl alcohols in one step. The negative fluorine effect in the nucleophilic fluoroalkylation of epoxides with fluorinated carbanions was probed by the reactivity comparison between carbanions PhSO2CF2- ( 3) and PhSO2CCl2- ( 4) and between carbanions PhSO2CHF- ( 7) and PhSO2CHCl- (13). The mediation of this fluorine effect by introducing another electron-withdrawing benzenesulfonyl group was found to be an effective way to significantly increase the nucleophilicity of the fluorinated carbanions, with the reactivity order [(PhSO2)(2)CF-] (16) > PhSO2CFH- (7) >> PhSO2CF2- ( 3).