Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction in Water Using Cyclodextrin as a Phase Transfer Catalyst

被引：148

作者：

Shin, Jung-Ah ^{[1
]}

Lim, Yeong-Gweon ^{[1
]}

Lee, Kyung-Hee ^{[1
]}

机构：

[1] Agcy Def Dev, Taejon 305600, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 08期

关键词：

BETA-CYCLODEXTRIN; PHARMACEUTICAL APPLICATIONS; 1,3-DIPOLAR CYCLOADDITIONS; HUISGEN CYCLOADDITION; INCLUSION COMPLEXES; TERMINAL ALKYNES; CLICK-CHEMISTRY; TRIAZOLE; IMPROVEMENT; LIGATION;

D O I：

10.1021/jo3000095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,4-Disubstituted-1,2,3-triazoles were obtained in excellent yields from azides and terminal alkynes in H2O in the presence of catalytic amount of beta-cyclodextrin as a phase transfer catalyst. Also, a one-pot CuAAC reaction was carried out successfully, affording 1,4-disubstituted-1,2,3-triazoles in good to high yields starting from an alkyl bromide, sodium azide, and terminal alkyne.

引用

收藏

页码：4117 / 4122

页数：6

相关论文

共 40 条

[1]

Bhosale SV, 2007, MINI-REV ORG CHEM, V4, P231

[2] Heterogeneous Catalytic Reactions "On Water" by Using Stable Polymeric Alkynylcopper(I) Pre-Catalysts: Alkyne/Azide Cycloaddition Reactions [J].

Buckley, Benjamin R. ;

Dann, Sandra E. ;

Heaney, Harry ;

Stubbs, Emma C. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (04) :770-776

[3] Phosphoramidite accelerated copper(I)-catalyzed [3+2] cycloadditions of azides and alkynes [J].

Campbell-Verduyn, Lachlan S. ;

Mirfeizi, Leila ;

Dierckx, Rudi A. ;

Elsinga, Philip H. ;

Feringa, Ben L. .

CHEMICAL COMMUNICATIONS, 2009, (16) :2139-2141

[4] Cyclodextrins in drug delivery: An updated review [J].

Challa, R ;

Ahuja, A ;

Ali, J ;

Khar, RK .

AAPS PHARMSCITECH, 2005, 6 (02)

[5]

Feng W., 2008, GREEN CHEM, V10, P452

[6] 1-Allyl- and 1-Benzyl-3-methyl-1,2,3-triazolium Salts via Tandem Click Transformations [J].

Fletcher, James T. ;

Keeney, Matthew E. ;

Walz, Sara E. .

SYNTHESIS-STUTTGART, 2010, (19) :3339-3345

[7] Studies on coumestrol/β-cyclodextrin characterization [J].

Franco, Camila ;

Schwingel, Liege ;

Lula, Ivana ;

Sinisterra, Ruben D. ;

Koester, Leticia Scherer ;

Bassani, Valquiria Linck .

INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2009, 369 (1-2) :5-11

[8] Reusable polymer-supported catalyst for the [3+2] Huisgen cycloaddition in automation protocols [J].

Girard, C ;

Önen, E ;

Aufort, M ;

Beauvière, S ;

Samson, E ;

Herscovici, J .

ORGANIC LETTERS, 2006, 8 (08) :1689-1692

[9] Effect of temperature on triazole and bistriazole formation through copper-catalyzed alkyne-azide cycloaddition [J].

Gonzalez, Jaime ;

Perez, Victor M. ;

Jimenez, David O. ;

Lopez-Valdez, German ;

Corona, David ;

Cuevas-Yanez, Erick .

TETRAHEDRON LETTERS, 2011, 52 (27) :3514-3517

[10] Dendronized linear polymers via "click chemistry" [J].

Helms, B ;

Mynar, JL ;

Hawker, CJ ;

Fréchet, JMJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15020-15021

← 1 2 3 4 →