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)2CF-] (16) > PhSO2CFH- (7) >> PhSO2CF2- (3).
Ni
Chuanfa
C
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Li
Ya
Y
Hu
Jinbo
J
D000838:Anions; D002625:Chemistry, Organic / Q000379:methods*; D004852:Epoxy Compounds / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry*
D000838:Anions; D004852:Epoxy Compounds; D006845:Hydrocarbons, Fluorinated; D013450:Sulfones