Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 1925-1938.DOI: 10.6023/cjoc202009035 Previous Articles     Next Articles



程步清a, 葛丹华a,*(), 汪欣b, 褚雪强a,*()   

  1. a 南京工业大学化学与分子工程学院 先进化学制造研究院 南京 211816
    b 湖北省地质实验测试中心 武汉 430034
  • 收稿日期:2020-09-15 修回日期:2020-11-12 发布日期:2020-12-01
  • 通讯作者: 葛丹华, 褚雪强
  • 基金资助:
    南京工业大学启动资金(39837146); 国家自然科学基金(22001121); 江苏省自然科学基金(BK20180690)

Perfluoroalkyl Halides as Fluorine-Containing Building Blocks for the Synthesis of Fluoroalkylated Heterocycles

Buqing Chenga, Danhua Gea,*(), Xin Wangb, Xueqiang Chua,*()   

  1. a Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816
    b Hubei Province Geological Experimental Testing Center, Wuhan 430034
  • Received:2020-09-15 Revised:2020-11-12 Published:2020-12-01
  • Contact: Danhua Ge, Xueqiang Chu
  • About author:
    * Corresponding authors. E-mail: ;
  • Supported by:
    Financial Support from Nanjing Tech University(39837146); National Natural Science Foundation of China(22001121); National Natural Science Foundation of Jiangsu Province(BK20180690)

The unique chemical and physical advantages conferred by incorporation of F-atoms/perfluoroalkyl groups (Rf) into organic compounds have gained widespread recognition throughout drug discovery, crop protection, polymer chemistry, and materials science. The past decades have witnessed a boom in organofluorine chemistry and heterocyclic chemistry mainly owing to the importance of fluorine-containing heterocycles. As a result, the exploitation of readily available fluorinated building blocks to attach Rf groups to various heterocycles has become an important topic in synthetic chemistry. On the other hand, perfluoroalkyl halide, as a low-toxic and environmentally friendly perfluoroalkyl building block, has been extensively utilized as a unique reagent in the heterocycle construction. Considering the great influence and synthetic potential of these novel avenues, we summarize the recent advances for the synthesis of fluoroalkylated heterocycles by using perfluoroalkyl halides as key fluorine-containing building blocks. One or three C—X bonds of perfluoroalkyl halides are cleaved/functiona- lized during the perfluoroalkylation and cyclization process, and a series of perfluoroalkylated heterocycles such as quinoxalines, phenanthridines, hydrazones, thiazoles, pyrimidines, aza-tricycles, isoxazoles,etc. were synthesized in moderate to good yields. With a specific emphasis on their proposed mechanism, we hope this review will be useful for medicinal and synthetic organic chemists who are interested in radical-mediated perfluoroalkylation.

Key words: perfluoroalkyl halide, fluorine-containing building block, fluoroalkylated heterocycle, cyclization, radical reaction