Nucleophilic fluoroalkylation of epoxides with fluorinated sulfones |
| |
| Authors: | Ni Chuanfa Li Ya Hu Jinbo |
| |
| Institution: | Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China. |
| |
| Abstract: | 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). |
| |
| Keywords: | |
| 本文献已被 PubMed 等数据库收录！ |
|
