Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (4): 1136-1145.DOI: 10.6023/cjoc202110003 Previous Articles     Next Articles



潘鹏a, 袁启洋a, 刘石惠b, 赵建宏a,*(), 张永强a,*()   

  1. a 华东理工大学药学院 上海 200237
    b 嘉兴学院医学院 浙江嘉兴 314001
  • 收稿日期:2021-10-02 修回日期:2021-12-23 发布日期:2022-01-11
  • 通讯作者: 赵建宏, 张永强
  • 作者简介:
    † 共同第一作者
  • 基金资助:

Research of Quinuclidine-Promoted C—H Silylation of Electron- Deficient Nitrogen Heteroarenes

Peng Pana, Qiyang Yuana, Shihui Liub, Jianhong Zhaoa(), Yongqiang Zhanga()   

  1. a School of Pharmacy, East China University of Science and Technology, Shanghai 200237
    b College of Medicine, Jiaxing University, Jiaxing, Zhejiang 314001
  • Received:2021-10-02 Revised:2021-12-23 Published:2022-01-11
  • Contact: Jianhong Zhao, Yongqiang Zhang
  • About author:
    † These authors contributed equally to this work.
  • Supported by:
    National Natural Science Foundation of China(21871086)

Herein, a novel quinuclidine-promoted C—H silylation reaction using ammonium persulfate as the oxidant and hydrosilane as the silyl sourse was reported. The protocol proceeds via the hydrogen atom transfer-based formation of silyl radical and features mild and green reaction conditions, operational-simplicity, relatively easy scale-up, broad substrate scope and good functional group compatibility, providing a powerful tool for the facile introduction of silyl groups on electron- deficient nitrogen heteroarenes. Furthermore, in combination with the C—Si bond-based coupling reactions, the new reaction also offers a verstile platform for the rapid modification of electon-deficient nitrogen heteroarenes.

Key words: quinuclidine, electron-deficient nitrogen heteroarenes, hydrogen atom transfer, silyl radical, C—H silylation