Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 1-14.DOI: 10.6023/cjoc201808030 Previous Articles     Next Articles

Special Issue: 庆祝陈庆云院士九十华诞



黄航a, 王兮a, 王剑波b   

  1. a 湖南大学化学化工学院 长沙 410082;
    b 北京大学化学与分子工程学院 北京 100871
  • 收稿日期:2018-08-27 修回日期:2018-11-21 发布日期:2018-11-30
  • 通讯作者: 王兮, 王剑波;
  • 基金资助:


Research Developments of the Construction of Chiral Center Based on Fluoroalkyl Radical Reactions

Huang Hanga, Wang Xia, Wang Jianbob   

  1. a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    b College of Chemistry and Molecular Engineering, Peking University, Beijing 100871
  • Received:2018-08-27 Revised:2018-11-21 Published:2018-11-30
  • Contact: 10.6023/cjoc201808030;
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21332002).

Fluorine-containing organic compounds have been widely applied in various fields, such as pharmacy, agrochemicals, materials science, etc. Trifluoromethyl, difluoromethyl and perfluoroalkyl groups represent the typical fluorine-containing functional groups. Hence, the development of highly efficient methods for introducing fluoroalkyl groups is of primary importance. In recent years, the reactions based on fluoroalkyl radicals have been developed into competent methods for introducing fluoroalkyl groups. On the other hand, the synthesis of the chiral molecules containing fluoroalkyl groups has attracted considerable attentions. However, attributed to the high reactivity of the fluoroalkyl radicals, the control of the reaction selectivity is difficult. Particularly, so far there have been only limited reports on the enantiocontrol of the reaction in this regard and the corresponding review of the field still lacks. This review summarizes the research on the asymmetric synthesis based on fluoroalkyl radical reactions developed over the past 20 years. The review introduces the selectivities, scope and mechanism of various reactions. It is divided into three different parts according to the type of the reaction: (1) asymmetric fluoroalkylation of enol/enamine intermediate through fluoroalkyl radical, (2) asymmetric difunctionalization of olefin through fluoroalkyl radical, (3) stereoselective 1,2-shift of vinylboronate complexes through fluoroalkyl radical.

Key words: fluoroalkylation, radicals, asymmetric synthesis, catalysis References