Sodium-iodide-promoted nickel-catalyzed C-N cross-coupling of aryl chlorides and N-nucleophiles under visible-light irradiation

被引：10

作者：

Feng, Yunhui ^{[1
]}

Luo, Hang ^{[1
]}

Yu, Fangnian ^{[1
]}

Liao, Qian ^{[1
]}

Lin, Luqing ^{[1
]}

机构：

[1] Dalian Univ Technol, Zhang Dayu Sch Chem, Dalian 116024, Liaoning, Peoples R China

来源：

GREEN CHEMISTRY | 2023年 / 25卷 / 06期

关键词：

AMINATION; COPPER; PHOTOREDOX; HALIDES;

D O I：

10.1039/d2gc04630j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report visible-light-promoted single nickel catalysis to smoothly achieve various C-N couplings of aryl chlorides/bromides and diverse N-nucleophiles with sodium iodide as the activator. Single nickel catalysts play two compatible roles: halogen exchange and C-N coupling, which are critical to successfully obtaining desired coupling products. The catalytic process does not need an exogenous photocatalyst and provides a sustainable and efficient approach to achieve C-N coupling under mild conditions. Experimental studies in combination with UV-vis and NMR analyses showed that the halogen exchange of both Ni-II and Ni-III-halide complexes with an iodide anion was a significant process for yielding the coupling products.

引用

页码：2361 / 2367

页数：7

共 46 条

[1] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[2] Kinetics of a Ni/Ir-Photocatalyzed Coupling of ArBr with RBr: Intermediacy of ArNiII(L)Br and Rate/Selectivity Factors [J].

Ben-Tal, Yael ;

Lloyd-Jones, Guy C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (33) :15372-15382

[3] Ullmann-Ma Reaction: Development, Scope and Applications in Organic Synthesis† [J].

Cai, Qian ;

Zhou, Wei .

CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (08) :879-893

[4]

Cavedon C, 2022, ANGEW CHEM INT EDIT, V61, DOI [10.1002/ange.202215123, 10.1002/anie.202215123, 10.1002/anie.202211433]

[5] Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis [J].

Chan, Amy Y. ;

Perry, Ian B. ;

Bissonnette, Noah B. ;

Buksh, Benito F. ;

Edwards, Grant A. ;

Frye, Lucas, I ;

Garry, Olivia L. ;

Lavagnino, Marissa N. ;

Li, Beryl X. ;

Liang, Yufan ;

Mao, Edna ;

Millet, Agustin ;

Oakley, James, V ;

Reed, Nicholas L. ;

Sakai, Holt A. ;

Seath, Ciaran P. ;

MacMillan, David W. C. .

CHEMICAL REVIEWS, 2022, 122 (02) :1485-1542

[6] Ni(II)-(σ-Aryl) complex:: A facile, efficient catalyst for nickel-catalyzed carbon-nitrogen coupling reactions [J].

Chen, Chen ;

Yang, Lian-Ming .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6324-6327

[7] Aryl amination using ligand-free Ni(II) salts and photoredox catalysis [J].

Corcoran, Emily B. ;

Pirnot, Michael T. ;

Lin, Shishi ;

Dreher, Spencer D. ;

DiRocco, Daniel A. ;

Davies, Ian W. ;

Buchwald, Stephen L. ;

MacMillan, David W. C. .

SCIENCE, 2016, 353 (6296) :279-283

[8] Photoinduced Ullmann C-N Coupling: Demonstrating the Viability of a Radical Pathway [J].

Creutz, Sidney E. ;

Lotito, Kenneth J. ;

Fu, Gregory C. ;

Peters, Jonas C. .

SCIENCE, 2012, 338 (6107) :647-651

[9]

Dorel R, 2019, ANGEW CHEM INT EDIT, V58, P17118, DOI [10.1002/ange.201904795, 10.1002/anie.201904795]

[10] A Unified and Practical Method for Carbon-Heteroatom Cross-Coupling using Nickel/Photo Dual Catalysis [J].

Escobar, Randolph A. ;

Johannes, Jeffrey W. .

CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (23) :5168-5173

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