Direct N-H Activation to Generate Nitrogen Radical for Arylamine Synthesis via Quantum Dots Photocatalysis

被引：24

作者：

Gan, Qi-Chao ^{[1
,2
,3
]}

Qiao, Jia ^{[1
,2
,3
]}

Zhou, Chao ^{[1
,2
,3
]}

Ci, Rui-Nan ^{[1
,2
,3
]}

Guo, Jia-Dong ^{[1
,2
,3
]}

Chen, Bin ^{[1
,2
,3
]}

Tung, Chen-Ho ^{[1
,2
,3
]}

Wu, Li-Zhu ^{[1
,2
,3
]}

机构：

[1] Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China

[2] Univ Chinese Acad Sci, Sch Future Technol, Beijing 100049, Peoples R China

[3] New Cornerstone Sci Lab, Shenzhen 518054, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 17期

基金：

中国国家自然科学基金; 国家重点研发计划;

关键词：

C-N Bond Formation; N-Radicals; N-H Activation; Quantum Dots; Visible Light Catalysis; CENTERED RADICALS; REGIOSELECTIVE AMINATION; BOND FORMATION; ARYL AMINES; IN-SITU; PHOTOREDOX; LIGHT; ARYLATION; ARENES; SALTS;

D O I：

10.1002/anie.202218391

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Represented herein is the first example of N-radical generation direct from N-H bond activation under mild and redox-neutral conditions. The in situ generated N-radical intercepts a reduced heteroarylnitrile/aryl halide for C-N bond formation under visible-light irradiation of quantum dots (QDs). A series of aryl and alkylamines with heteroarylnitriles/aryl halides exhibit high efficiency, site-selectivity and good functional-group tolerance. Moreover, consecutive C-C and C-N bond formation using benzylamines as substrates is also achieved, producing N-aryl-1,2-diamines with H-2 evolution. The redox-neutral conditions, broad substrate scope, and efficiency of N-radical formation are advantageous for organic synthesis.

引用

页数：7

共 127 条

[1] N-Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible Light Photocatalyzed Room Temperature C-H Amination of Arenes and Heteroarenes [J].