Synthesis of Quinoxalines through Cu-electrocatalytic Azidation/Annulation Cascade at Low Catalyst Loading

被引：21

作者：

Baidya, Mrinmay ^{[1
]}

De Sarkar, Suman ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741246, West Bengal, India

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 31期

关键词：

ELECTROCHEMICAL DIAZIDATION; BOND-CLEAVAGE; EASY ACCESS; AZIDATION; RADICALS; ALKENES;

D O I：

10.1021/acs.orglett.3c02186

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Cu-electrocatalytic azidation of N-aryl enaminesand subsequent denitrogenative annulation for the construction ofquinoxaline frameworks is reported. Only 0.5 mol % of copper(II) chloridewas employed for this cascade transformation displaying excellentfunctional-group compatibility even with complex bioactive scaffolds.The efficient electro-oxidative protocol enables the use of NaN3 as the cheapest azide source. Detailed mechanistic experiments,cyclic voltammetry, and spectroscopic studies provided strong evidencefor a dual role of the Cu catalyst in azidyl and iminyl radical generationsteps.

引用

收藏

页码：5896 / 5901

页数：6

相关论文

共 43 条

[1] Electrochemical Organoselenium Catalysis for the Selective Activation of Alkynes: Easy Access to Carbonyl-pyrroles/oxazoles from N-Propargyl Enamines/Amides [J].

Baidya, Mrinmay ;

Dutta, Jhilik ;

De Sarkar, Suman .

ORGANIC LETTERS, 2023, 25 (20) :3812-3817

[2] Trifluoroethanol as a Unique Additive for the Chemoselective Electrooxidation of Enamines to Access Unsymmetrically Substituted NH-Pyrroles [J].

Baidya, Mrinmay ;

Maiti, Debabrata ;

Roy, Lisa ;

De Sarkar, Suman .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (05)

[3] Photochemical diazidation of alkenes enabled by ligand-to-metal charge transfer and radical ligand transfer [J].

Bian, Kang-Jie ;

Kao, Shih-Chieh ;

Nemoto, David, Jr. ;

Chen, Xiao-Wei ;

West, Julian G. .

NATURE COMMUNICATIONS, 2022, 13 (01)

[4]

Bra''se S., 2009, ORGANIC AZIDES SYNTH

[5] Cu-Electrocatalytic Diazidation of Alkenes at ppm Catalyst Loading [J].

Cai, Chen-Yan ;

Zheng, Yun-Tao ;

Li, Jing-Fu ;

Xu, Hai-Chao .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (27) :11980-11985

[6] Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts [J].

Cai, Yuan ;

Chatterjee, Sagnik ;

Ritter, Tobias .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (25) :13542-13548

[7] Radical annulations with nitriles: Novel cascade reactions of cyano-substituted alkyl and sulfanyl radicals with isonitriles [J].

Camaggi, CM ;

Leardini, R ;

Nanni, D ;

Zanardi, G .

TETRAHEDRON, 1998, 54 (21) :5587-5598

[8] Copper-Catalyzed Synthesis of Azaspirocyclohexadienones from α-Azido-N-arylamides under an Oxygen Atmosphere [J].

Chiba, Shunsuke ;

Zhang, Line ;

Lee, Jian-Yuan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7266-+

[9] Generation of Iminyl Copper Species from α-Azido Carbonyl Compounds and Their Catalytic C-C Bond Cleavage under an Oxygen Atmosphere [J].

Chiba, Shunsuke ;

Zhang, Line ;

Ang, Gim Yean ;

Hui, Benjamin Wei-Qiang .

ORGANIC LETTERS, 2010, 12 (09) :2052-2055

[10] A copper catalyzed azidation and peroxidation of β-naphthols via an oxidative dearomatization strategy [J].

Dhineshkumar, Jayaraman ;

Samaddar, Prasanjit ;

Prabhu, Kandikere Ramaiah .

CHEMICAL COMMUNICATIONS, 2016, 52 (74) :11084-11087

← 1 2 3 4 5 →