Sequential One-Pot Ruthenium-Catalyzed Azide-Alkyne Cycloaddition from Primary Alkyl Halides and Sodium Azide

被引：97

作者：

Johansson, Johan R. ^{[1
]}

Lincoln, Per ^{[1
]}

Norden, Bengt ^{[1
]}

Kann, Nina ^{[1
]}

机构：

[1] Chalmers, Dept Chem & Biol Engn, Div Chem & Biochem, SE-41296 Gothenburg, Sweden

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 07期

关键词：

CLICK CHEMISTRY; TERMINAL ALKYNES; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; TRIAZOLE LINKAGES; ORGANIC AZIDES; DIVERSITY; ANALOGS; AMINES; SCOPE;

D O I：

10.1021/jo200134a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An experimentally simple sequential one-pot RuAAC reaction, affording 1,5-disubstituted 1H-1,2,3-triazoles in good to excellent yields starting from; an alkyl halide, sodium azide, and an alkyne, is reported. The organic azide is formed in situ by treating the primary alkyl halide with sodium azide in DMA under microwave heating. Subsequent addition of [RuClCp*-(PPh3)(2)] and the alkyne yielded the desired cycloaddition product after further microwave irradiation.

引用

页码：2355 / 2359

页数：5

共 32 条

[1] 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

[2] Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages [J].

Barral, Karine ;

Moorhouse, Adam D. ;

Moses, John E. .

ORGANIC LETTERS, 2007, 9 (09) :1809-1811

[3] One-pot procedure for diazo transfer and azide-alkyne cycloaddition: Triazole linkages from amines [J].

Beckmann, Henning S. G. ;

Wittmann, Valentin .

ORGANIC LETTERS, 2007, 9 (01) :1-4

[4] 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

[5] Preparation of Polymers Containing Metal-Metal Bonds along the Backbone Using Click Chemistry [J].

Brady, Sarah E. ;

Shultz, Ginger V. ;

Tyler, David R. .

JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS, 2010, 20 (03) :511-518

[6] 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

[7] Phenylthiomethyl Glycosides: Convenient Synthons for the Formation of Azidomethyl and Glycosylmethyl Glycosides and Their Derivatives [J].

Crich, David ;

Yang, Fan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (47) :8896-8899

[8] Dimerization of terminal alkynes catalyzed by chloro(η5-pentadienyl) bis(triphenylphosphine)ruthenium(II) and kinetics of phosphine substitution [J].

Daniels, Matthew ;

Kirss, Rein U. .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (08) :1716-1725

[9] One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides [J].

Feldman, AK ;

Colasson, B ;

Fokin, VV .

ORGANIC LETTERS, 2004, 6 (22) :3897-3899

[10] Click chemistry: function follows form [J].

Finn, M. G. ;

Fokin, Valery V. .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (04) :1231-1232

← 1 2 3 4 →