Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (12): 2604-2609.DOI: 10.6023/cjoc201506014 Previous Articles     Next Articles



李青巍a, 陈福利a, 杨先金a,b   

  1. a 华东理工大学精细化工研究所结构可控先进功能材料及其制备教育部重点实验室 上海 200327;
    b 中国科学院上海有机化学研究所有机氟化学重点实验室 上海 200327
  • 收稿日期:2015-06-12 修回日期:2015-07-13 发布日期:2015-08-17
  • 通讯作者: 杨先金
  • 基金资助:

    国家自然科学基金(No. 2132077)资助项目.

Synthesis of Substituted N—F Benzenesulfonimides and Comparison of Their Fluorination Reactivity via Their Reactions with Silylenol Ethers

Li Qingweia, Chen Fulia, Yang Xianjina,b   

  1. a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237;
    b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2015-06-12 Revised:2015-07-13 Published:2015-08-17
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 2132077).

The fluorination reactivity of N—F benzenesulfonimides depended on the strength of N—F bond and was easily affected by substituents on the phenyl of substituted N—F benzenesulfonimides via electronic or steric effect. In this work, N—F benzenesulfonimides with different substituents were synthesized and reacted with silylenol ethers, and the results indicated that utilizing N-fluoro-4-fluoro-4'-nitrobenzenesulfonimide and N-fluoro-4-tert-butyl-4'-fluorobenzenesulfonimide could improve the reactivity or selectivity of fluorination than using N—F benzenesulfonimide in lots of selected experiments.

Key words: substituted N—F benzenesulfonimide, fluorination, silylenol ether