Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1483-1491.DOI: 10.6023/cjoc202208031 Previous Articles     Next Articles

Special Issue: 有机氟化学虚拟合辑



梁志鹏a, 叶浩a, 张海滨b, 姜国民a,*(), 吴新星a,c,*()   

  1. a 南通大学化学化工学院 江苏南通 226019
    b 南通职业大学药品与环境工程学院 江苏南通 226019
    c 江苏浩丰生物科技有限公司 江苏南通 226019
  • 收稿日期:2022-08-24 修回日期:2022-11-02 发布日期:2022-12-07
  • 通讯作者: 姜国民, 吴新星
  • 基金资助:
    国家自然科学基金(22201145); 南通大学高层次人才科研基金(03083031); 江苏省高校自然科学研究(21KJB150015); 南通大学大型仪器开放基金(KFJN2215)

Ring Opening Amination of gem-Difluorocyclopropanes with Cyclobutanone Hydrazones

Zhipeng Lianga, Hao Yea, Haibin Zhangb, Guomin Jianga(), Xinxing Wua,c()   

  1. a College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019
    b College of Pharmaceutical and Environmental Engineering, Nantong Vocational University, Nantong, Jiangsu 226019
    c Jiangsu Haofeng Bio-technology Co., Ltd., Nantong, Jiangsu 226019
  • Received:2022-08-24 Revised:2022-11-02 Published:2022-12-07
  • Contact: Guomin Jiang, Xinxing Wu
  • Supported by:
    National Natural Science Foundation of China(22201145); Scientific Research Foundation of High-level Talents of Nantong University(03083031); Universities Natural Science Research Project of Jiangsu Province(21KJB150015); Large Instruments Open Foundation of Nantong University(KFJN2215)

N-Fluoroallyl hydrazones with four-ring structure were effectively synthesized using cyclobutanone hydrazones and gem-difluorocyclopropanes as raw materials through palladium catalyzed ring opening of difluorocyclopropanes and nucleophilic capture process of nitrogen nucleophile. This protocol shows broad substrate scope and good functional group tolerance, which can be applied for gram-scale preparation.

Key words: cyclobutanone hydrazone, gem-difluorocyclopropane, ring opening reaction, monofluoroalkene