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

[11]

Elks J., 1972, CHEM ABSTR, V76

[12] Room-temperature Cu(II)-catalyzed aromatic C-H azidation for the synthesis of ortho-azido anilines with excellent regioselectivity [J].

Fan, Yunpeng ;

Wan, Wen ;

Ma, Guobin ;

Gao, Wei ;

Jiang, Haizhen ;

Zhu, Shizheng ;

Hao, Jian .

CHEMICAL COMMUNICATIONS, 2014, 50 (43) :5733-5736

[13] Sensitivities of Some Imidazole-1-sulfonyl Azide Salts [J].

Fischer, Niko ;

Goddard-Borger, Ethan D. ;

Greiner, Robert ;

Klapoetke, Thomas M. ;

Skelton, Brian W. ;

Stierstorfer, Joerg .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (04) :1760-1764

[14] Carbon-fluorine reductive elimination from a high-valent palladium fluoride [J].

Furuya, Takeru ;

Ritter, Tobias .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (31) :10060-+

[15] An efficient, inexpensive, and shelf-stable diazotransfer reagent: Imidazole-1-sulfonyl azide hydrochloride [J].

Goddard-Borger, Ethan D. ;

Stick, Robert V. .

ORGANIC LETTERS, 2007, 9 (19) :3797-3800

[16] Copper-catalysed azide-alkyne cycloadditions (CuAAC): an update [J].

Haldon, Estela ;

Carmen Nicasio, M. ;

Perez, Pedro J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (37) :9528-9550

[17] Practical Azidation of 1,3-Dicarbonyls [J].

Harschneck, Tobias ;

Hummel, Sara ;

Kirsch, Stefan F. ;

Klahn, Philipp .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (04) :1187-1193

[18] Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides [J].

Hein, Jason E. ;

Fokin, Valery V. .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (04) :1302-1315

[19] Efficient synthesis of 2-substituted-1,2,3-triazoles [J].

Kalisiak, Jaroslaw ;

Sharpless, K. Barry ;

Fokin, Vallery V. .

ORGANIC LETTERS, 2008, 10 (15) :3171-3174

[20] Benzotriazol-1-yl-sulfonyl Azide for Diazotransfer and Preparation of Azidoacylbenzotriazoles [J].

Katritzky, Alan R. ;

El Khatib, Mirna ;

Bol'shakov, Oleg ;

Khelashvili, Levan ;

Steel, Peter J. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (19) :6532-6539

← 1 2 3 4 5 6 7 →