Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (1): 133-139.DOI: 10.6023/cjoc201907002 Previous Articles     Next Articles

可见光促进三级胺α位C(sp3)—H键的胺化反应研究

赵亚婷a,b, 曾俊杰b, 夏吾炯b   

  1. a 衢州学院化学与材料工程学院 浙江衢州 324000;
    b 哈尔滨工业大学(深圳)城市水资源与水环境国家重点实验室 广东深圳 518055
  • 收稿日期:2019-07-02 修回日期:2019-08-20 出版日期:2020-01-25 发布日期:2019-09-05
  • 通讯作者: 赵亚婷, 夏吾炯 E-mail:liveagain@126.com;xiawj@hit.edu.cn
  • 基金资助:
    国家自然科学基金(Nos.21901141,21672047)和衢州学院科研启动基金(No.BSYJ201714)资助项目.

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

Zhao Yatinga,b, Zeng Junjieb, Xia Wujiongb   

  1. 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:2019-07-02 Revised:2019-08-20 Online:2020-01-25 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).

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