Copper-catalysed regioselective azidation of arenes by C-H activation directed by pyridine

被引：12

作者：

Azad, Chandra S. ^{[1
]}

Narula, Anudeep K. ^{[1
]}

机构：

[1] GGS Indraprastha Univ, Hygeia Ctr Excellence Pharmaceut Sci CEPS, New Delhi 110078, India

来源：

RSC ADVANCES | 2015年 / 5卷 / 121期

关键词：

CLICK CHEMISTRY; ORTHO-NITRATION; BOND; AZIDE; C(SP(2))-H; ALKYNE; FUNCTIONALIZATION; DIAZOTRANSFER; CONSTRUCTION; CARBOLINES;

D O I：

10.1039/c5ra21963a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel and efficient copper-catalysed pyridine directed ortho-azidation of arenes has been developed using safe and stable benzotriazole sulphonyl azide as the azidating agent. A variety of organo azides have been synthesized with electron donor and withdrawing groups, thereby the azide products can be easily transformed into assorted functionalities.

引用

页码：100223 / 100227

页数：5

共 68 条

[1] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[2] Operative conversions of 3-carboxy-4-quinolones into 3-nitro-4-quinolones via ipso-nitration: potential antifilarial agents as inhibitors of Brugia malayi thymidylate kinase [J].

Azad, Chandra S. ;

Balaramnavar, Vishal M. ;

Khan, Imran A. ;

Doharey, Pawan K. ;

Saxena, Jitendra K. ;

Saxena, Anil K. .

RSC ADVANCES, 2015, 5 (100) :82208-82214

[3] Organic azides:: An exploding diversity of a unique class of compounds [J].

Bräse, S ;

Gil, C ;

Knepper, K ;

Zimmermann, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240

[4]

Brase S., 2010, Organic Azides, Syntheses and Applications

[5] 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

[6]

Chu C. K., 2005, US Patent, Patent No. [US 6949521 B2, 6949521]

[7] Enantioselective Iron-Catalyzed Azidation of β-Keto Esters and Oxindoles [J].

Deng, Qing-Hai ;

Bleith, Tim ;

Wadepohl, Hubert ;

Gade, Lutz H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5356-5359

[8] Hypervalent iodine(III): selective and efficient single-electron-transfer (SET) oxidizing agent [J].

Dohi, Toshifumi ;

Ito, Motoki ;

Yamaoka, Nobutaka ;

Morimoto, Koji ;

Fujioka, Hiromichi ;

Kita, Yasuyuki .

TETRAHEDRON, 2009, 65 (52) :10797-10815

[9] Hypervalent iodine reagents as a new entrance to organocatalysts [J].

Dohi, Toshifumi ;

Kita, Yasuyuki .

CHEMICAL COMMUNICATIONS, 2009, (16) :2073-2085

[10] Palladium-Catalyzed Direct Ortho-Nitration of Azoarenes Using NO2 as Nitro Source [J].

Dong, Jiawei ;

Jin, Bo ;

Sun, Peipei .

ORGANIC LETTERS, 2014, 16 (17) :4540-4542

← 1 2 3 4 5 6 7 →