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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 1: 133 - 139

DOI: https://doi.org/10.6023/cjoc201907002

Visible-Light-Induced α-C(sp3)—H Amination Reactions of Tertiary Amines

  • Zhao Yating ,
  • Zeng Junjie ,
  • Xia Wujiong
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  • a College of Chemical and Material Engineering, Quzhou University, Quzhou, Zhejiang 324000;
    b State Key Laboratory of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology[Shenzhen], Shenzhen, Guangdong 518055

Received date: 2019-07-02

  Revised date: 2019-08-20

  Online published: 2019-09-05

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21901141, 21672047), and the Start-up Funds of Quzhou University (No. BSYJ201714).

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Abstract

Herein, the visible-light-induced α-C(sp3)—H amination reactions of tertiary amines were reported. By using readily available 1,3-dioxoisoindolin-2-yl benzoate as precursor of N-radical and blue LEDs as green and sustainable energy source, the α-C(sp3)—H bonds of various N,N-dimethylaniline derivatives were aminated directly. Based on radical trapping experiment and documented literature, a mechanism involving radicals coupling was proposed. This method featured in mild reaction conditions and good functional group tolerance, which provides a simple and practical protocol to the modification of tertiary amines.

Key words： photoredox catalysis; N-radical; amination reaction; C—H functionalization; radicals coupling

Cite this article

Zhao Yating , Zeng Junjie , Xia Wujiong . Visible-Light-Induced α-C(sp3)—H Amination Reactions of Tertiary Amines[J]. Chinese Journal of Organic Chemistry, 2020 , 40(1) : 133 -139 . DOI: 10.6023/cjoc201907002

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