Copper-Catalyzed Azide-Alkyne Cycloaddition: Regioselective Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles

被引：220

作者：

Spiteri, Christian ^{[1
]}

Moses, John E. ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 01期

关键词：

azides; click chemistry; cycloaddition; iodoalkynes; iodotriazoles; CLICK-CHEMISTRY; EFFICIENCY; LIGATION;

D O I：

10.1002/anie.200905322

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Clicking along nicely: Few methods have been reported to be an efficient entry to trisubstituted triazoles with high regioselectivity. This challenge has inspired a search tor new reactivity and the development of new chemical approaches. The development of an efficient robust onepot procedure as a route to highly decorated trisubstituted triazoles will be an added bonus to the range of click reactions (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KCaA.

引用

页码：31 / 33

页数：3

共 36 条

[1] Copper-mediated nucleophilic displacement reactions of 1-haloalkynes. Halogen-halogen exchange and sulfonylation [J].

Abe, H ;

Suzuki, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1999, 72 (04) :787-798

[2] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].

Bock, VD ;

Hiemstra, H ;

van Maarseveen, JH .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68

[3] Ruthenium-catalyzed azide-alkyne cycloaddition: Scope and mechanism [J].

Boren, Brant C. ;

Narayan, Sridhar ;

Rasmussen, Lars K. ;

Zhang, Li ;

Zhao, Haitao ;

Lin, Zhenyang ;

Jia, Guochen ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) :8923-8930

[4] Synthesis of 1,4,5-trisubstituted-1,2,3-triazoles by copper-catalyzed cycloaddition-coupling of azides and terminal alkynes [J].

Gerard, Baudouin ;

Ryan, Jamie ;

Beeler, Aaron B. ;

Porco, John A., Jr. .

TETRAHEDRON, 2006, 62 (26) :6405-6411

[5] Bringing efficiency to materials synthesis: The philosophy of click chemistry [J].

Hawker, Craig J. ;

Fokin, Valery V. ;

Finn, M. G. ;

Sharpless, K. Barry .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2007, 60 (06) :381-383

[6]

Hein J.E., 2009, Angew. Chem, V121, P8162, DOI DOI 10.1002/ANGE.200903558

[7] Copper(I)-Catalyzed Cycloaddition of Organic Azides and 1-Iodoalkynes [J].

Hein, Jason E. ;

Tripp, Jonathan C. ;

Krasnova, Larissa B. ;

Sharpless, K. Barry ;

Fokin, Valery V. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) :8018-8021

[8] Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates [J].

Himo, F ;

Lovell, T ;

Hilgraf, R ;

Rostovtsev, VV ;

Noodleman, L ;

Sharpless, KB ;

Fokin, VV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :210-216

[9]

Kolb H.C., 2001, ANGEW CHEM, V113, P2056, DOI 10.1002/1521-3757(20010601)113:11

[10] The growing impact of click chemistry on drug discovery [J].

Kolb, HC ;

Sharpless, KB .

DRUG DISCOVERY TODAY, 2003, 8 (24) :1128-1137

← 1 2 3 4 →