Copper(II)-Catalyzed Oxidative Cross-Coupling of Anilines, Primary Alkyl Amines, and Sodium Azide Using TBHP: A Route to 2-Substituted Benzimidazoles

被引：69

作者：

Mahesh, Devulapally ^{[1
]}

Sadhu, Pradeep ^{[1
]}

Punniyamurthy, Tharmalingam ^{[1
]}

机构：

[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 08期

关键词：

C-H AMINATION; N BOND FORMATION; SUBSTITUTED BENZIMIDAZOLES; ONE-POT; 1,2-DISUBSTITUTED BENZIMIDAZOLES; BIOLOGICAL EVALUATION; ARYL BENZIMIDAZOLES; CATALYZED SYNTHESIS; ALIPHATIC-AMINES; HIGHLY EFFICIENT;

D O I：

10.1021/acs.joc.6b00186

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper(II)-catalyzed oxidative cross-coupling of anilines, primary alkyl amines, and sodium azide is described in the presence of TBHP at moderate temperature. This one-pot multicomponent protocol involves a domino C-H functionalization, transimination, ortho-selective amination, and a cyclization sequence. The broad substrate scope and functional group compatibility are the significant practical features. The protocol can be extended to the coupling of benzyl alcohols with moderate yields.

引用

页码：3227 / 3234

页数：8

共 73 条

[1] [RhCp*Cl2]2-Catalyzed Directed N-Boc Amidation of Arenes "on Water" [J].

Ali, Md Ashif ;

Yao, Xiayin ;

Sun, Hao ;

Lu, Hongjian .

ORGANIC LETTERS, 2015, 17 (06) :1513-1516

[2] Organocatalytic Syntheses of Benzoxazoles and Benzothiazoles using Aryl Iodide and Oxone via C-H Functionalization and C-O/S Bond Formation [J].

Alla, Santhosh Kumar ;

Sadhu, Pradeep ;

Punniyamurthy, Tharmalingam .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16) :7502-7511

[3] Transition-Metal-Free Synthesis of Benzimidazoles Mediated by KOH/DMSO [J].

Baars, Hannah ;

Beyer, Astrid ;

Kohlhepp, Stefanie V. ;

Bolm, Carsten .

ORGANIC LETTERS, 2014, 16 (02) :536-539

[4] Copper(II)-Catalyzed Direct Dioxygenation of Alkenes with Air and N-Hydroxyphthalimide: Synthesis of β-Keto-N-alkoxyphthalimides [J].

Bag, Raghunath ;

Sar, Dinabandhu ;

Punniyamurthy, Tharmalingam .

ORGANIC LETTERS, 2015, 17 (08) :2010-2013

[5] Acylsilanes in Rhodium(III)-Catalyzed Directed Aromatic C-H Alkenylations and Siloxycarbene Reactions with C-C Double Bonds [J].

Becker, Peter ;

Priebbenow, Daniel L. ;

Pirwerdjan, Ramona ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :269-271

[6] Catalytic synthesis of aldehydes and ketones under mild conditions using TEMPO/Oxone [J].

Bolm, C ;

Magnus, AS ;

Hildebrand, JP .

ORGANIC LETTERS, 2000, 2 (08) :1173-1175

[7] An improved procedure for the synthesis of benzimidazoles, using palladium-catalyzed aryl-amination chemistry [J].

Brain, CT ;

Steer, JT .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6814-6816

[8] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].

Brasche, Gordon ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934

[9] Developments Towards Regioselective Synthesis of 1,2-Disubstituted Benzimidazoles [J].

Carvalho, Luisa C. R. ;

Fernandes, Eduarda ;

Marques, M. Manuel B. .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (45) :12544-12555

[10] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

← 1 2 3 4 5 6 7 8 →