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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 4: 1136 - 1145

DOI: https://doi.org/10.6023/cjoc202110003

ARTICLES

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

  • Peng Pan ,
  • Qiyang Yuan ,
  • Shihui Liu ,
  • Jianhong Zhao ,
  • Yongqiang Zhang
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  • a School of Pharmacy, East China University of Science and Technology, Shanghai 200237
    b College of Medicine, Jiaxing University, Jiaxing, Zhejiang 314001
† These authors contributed equally to this work.
* E-mail: ;

Received date: 2021-10-02

  Revised date: 2021-12-23

  Online published: 2022-01-11

Supported by

National Natural Science Foundation of China(21871086)

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Abstract

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

Cite this article

Peng Pan , Qiyang Yuan , Shihui Liu , Jianhong Zhao , Yongqiang Zhang . Research of Quinuclidine-Promoted C—H Silylation of Electron- Deficient Nitrogen Heteroarenes[J]. Chinese Journal of Organic Chemistry, 2022 , 42(4) : 1136 -1145 . DOI: 10.6023/cjoc202110003

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