Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 18, Pages 6829-6833Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo060955l
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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).
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