Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (11): 3562-3587.DOI: 10.6023/cjoc202204060 Previous Articles     Next Articles

Special Issue: 有机氟化学虚拟合辑

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二氟烯醇硅醚作为含氟砌块在构建有机氟化物中的研究进展

郭檬檬a, 于子伦a, 陈玉兰a, 葛丹华a,*(), 马猛涛b, 沈志良a, 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南京林业大学理学院 南京 210037
  • 收稿日期:2022-04-25 修回日期:2022-06-24 发布日期:2022-07-13
  • 通讯作者: 葛丹华, 褚雪强
  • 作者简介:
    †作者对文章贡献一致
  • 基金资助:
    南京工业大学(39837146); 南京工业大学(39837118); 国家自然科学基金(22001121); 江苏省自然科学基金(BK20180690)

Difluorinated Silyl Enol Ethers as Fluorine-Containing Building Blocks for the Synthesis of Organofluorine Compounds

Mengmeng Guoa, Zilun Yua, Yulan Chena, Danhua Gea(), Mengtao Mab, Zhiliang Shena, Xueqiang Chua()   

  1. aInstitute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816
    bCollege of Science, Nanjing Forestry University, Nanjing 210037
  • Received:2022-04-25 Revised:2022-06-24 Published:2022-07-13
  • Contact: Danhua Ge, Xueqiang Chu
  • About author:
    †These authors contributed equally to this work.
  • Supported by:
    Nanjing Tech University(39837146); Nanjing Tech University(39837118); National Natural Science Foundation of China(22001121); National Natural Science Foundation of Jiangsu Province(BK20180690)

Organofluorine compounds have been widely applied in various fields ranging from drug discovery, clinical medicines, agrochemistry, and materials science to organic synthesis, due to their special chemical and physical properties when compared with nonfluorinated analogs. In the past decades, significant progress has been made in the development of selective fluorination and fluoroalkylation for the synthesis of structurally diverse fluorine-containing molecules. Among them, the α-fluoroalkylated carbonyl group represents an important class of scaffold components in biologically active and druglike compounds. In this context, based on the use of difluorinated silyl enol ether (DFSEE) as a unique fluoroaklylating reagent, a variety of methods for the incorporation of gem-difluoroalkylated carbonyl moiety have been achieved, including aldol, Mannich, arylation, allylation, protonation, halogenation, conjugate addition, and olefination reactions. On the other hand, DFSEEs could also merge with new types of reactions such as radical-type difluoroalkylation and cascade reaction by virtue of their incredible reactive flexibility. In addition, the O-site selective addition of DFSEEs was also reported, enabling the construction of versatile gem-difluoroalkenes. Given the importance of organofluorine compounds and the synthetic potential of these avenues, herein, we highlight the recent advances in the functionalization of gem-difluorinated silyl enol ethers, which serve as key fluorine-containing building blocks for the synthesis of organofluorine compounds.

Key words: difluorinated silyl enol ether, fluorine-containing building block, fluorinated compounds, difluoroalkylation, organofluorine chemistry