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

doi:10.6023/cjoc201907002

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

Special Issue: 有机光催化虚拟合辑

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

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 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 Yating^a,b, Zeng Junjie^b, Xia Wujiong^b

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 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

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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.

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可见光促进三级胺α位C(sp³)—H键的胺化反应研究

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

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可见光促进三级胺α位C(sp3)—H键的胺化反应研究