One-Pot Click Synthesis of 1N-Alkyl-4-aryl-1,2,3-triazoles from Protected Arylalkynes and Alkyl Bromides

被引：32

作者：

Ladouceur, Sebastien ^{[1
]}

Soliman, Ahmed M. ^{[1
]}

Zysman-Colman, Eli ^{[1
]}

机构：

[1] Univ Sherbrooke, Dept Chim, Sherbrooke, PQ J1K 2R1, Canada

来源：

SYNTHESIS-STUTTGART | 2011年 / 22期

基金：

加拿大自然科学与工程研究理事会;

关键词：

click chemistry; Huisgen cycloaddition; triazoles; alkynes; azides; RHENIUM TRICARBONYL COMPLEXES; SITU GENERATED AZIDES; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; TERMINAL ALKYNES; 1,3-DIPOLAR CYCLOADDITIONS; REGIOSELECTIVE SYNTHESIS; RUTHENIUM(II) COMPLEXES; IRIDIUM(III) COMPLEXES; COUPLING REACTION; LIGANDS;

D O I：

10.1055/s-0030-1260256

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1N-Alkyl-4-aryl-1,2,3-triazoles have been prepared through a multicomponent one-pot protocol from the corresponding (arylethynyl)trimethylsilanes and alkyl bromides. In situ alkyl azide formation and alkyne deprotection followed by copper(I)-catalyzed click cycloaddition afforded the desired 1,4-disubstituted 1,2,3-triazoles in generally good to excellent yield, with only minor observation of the undesired 1,5-regioisomeric cycloadduct. The protocol eliminates the need to use reactive organic azides and terminal alkynes.

引用

页码：3604 / 3611

页数：8

共 60 条

[1]

[Anonymous], 2007, QSAR Comb. Sci, V26, P1111

[2] A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction [J].

Appukkuttan, P ;

Dehaen, W ;

Fokin, VV ;

Van der Eycken, E .

ORGANIC LETTERS, 2004, 6 (23) :4223-4225

[3] Tris(triazolyl)triazine via Click-Chemistry: A C3 Electron-Deficient Core with Liquid Crystalline and Luminescent Properties [J].

Beltran, Eduardo ;

Luis Serrano, Jose ;

Sierra, Teresa ;

Gimenez, Raquel .

ORGANIC LETTERS, 2010, 12 (07) :1404-1407

[4] Phenyl-1H-[1,2,3]triazoles as New Cyclometallating Ligands for Iridium(III) Complexes [J].

Beyer, Beatrice ;

Ulbricht, Christoph ;

Escudero, Daniel ;

Friebe, Christian ;

Winter, Andreas ;

Gonzalez, Leticia ;

Schubert, Ulrich S. .

ORGANOMETALLICS, 2009, 28 (18) :5478-5488

[5] 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

[6] 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

[7] Polytriazoles as copper(I)-stabilizing ligands in catalysis [J].

Chan, TR ;

Hilgraf, R ;

Sharpless, KB ;

Fokin, VV .

ORGANIC LETTERS, 2004, 6 (17) :2853-2855

[8] Rhenium tricarbonyl complexes of 1-benzyl-4-(5-bipyridyl)-1H-1,2,3-triazoles [J].

Cote, Catherine ;

Kirss, Rein U. .

INORGANICA CHIMICA ACTA, 2010, 363 (11) :2520-2525

[9] A multicomponent CuAAC "click" approach to a library of hybrid polydentate 2-pyridyl-1,2,3-triazole ligands: new building blocks for the generation of metallosupramolecular architectures [J].

Crowley, James D. ;

Bandeen, Pauline H. .

DALTON TRANSACTIONS, 2010, 39 (02) :612-623

[10] A one pot multi-component CuAAC "click" approach to bidentate and tridentate pyridyl-1,2,3-triazole ligands: Synthesis, X-ray structures and copper(II) and silver(I) complexes [J].

Crowley, James D. ;

Bandeen, Pauline H. ;

Hanton, Lyall R. .

POLYHEDRON, 2010, 29 (01) :70-83

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