Nucleophilic Fluoroalkylation of Epoxides with Fluorinated Sulfones
- 5 August 2006
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 71 (18), 6829-6833
- https://doi.org/10.1021/jo060955l
Abstract
The unprecedented nucleophilic fluoroalkylation of simple epoxides with fluorinated sulfones was achieved to give the β-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).Keywords
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