Multicomponent Synthesis of 1,2,3-Triazoles in Water Catalyzed by Copper Nanoparticles on Activated Carbon

被引：218

作者：

Alonso, Francisco ^{[1
,2
]}

Moglie, Yanina ^{[1
,2
]}

Radivoy, Gabriel ^{[3
]}

Yus, Miguel ^{[1
,2
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

[2] Univ Alicante, Inst Sintesis Organ, E-03080 Alicante, Spain

[3] Univ Nacl Sur, Inst Quim Sur INQUISUR CONICET, Dept Quim, RA-8000 Bahia Blanca, Buenos Aires, Argentina

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 18期

关键词：

click chemistry; copper nanoparticles; cycloaddition; heterogeneous catalysis; triazoles; water; ONE-POT SYNTHESIS; CLICK CHEMISTRY; TERMINAL ALKYNES; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; REGIOSELECTIVE SYNTHESIS; REUSABLE CATALYST; IN-SITU; 1,3-DIPOLAR CYCLOADDITIONS; SUPPORTED COPPER(I); MEDICINAL CHEMISTRY;

D O I：

10.1002/adsc.201000637

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Copper nanoparticles on activated carbon have been found to effectively catalyze the multicomponent synthesis of 1,2,3-triazoles from different azide precursors, such as organic halides, diazonium salts, anilines and epoxides in water. The first one-pot transformation of an olefin into a triazole is also described. The catalyst is easy to prepare, very versatile and reusable at a low copper loading.

引用

页码：3208 / 3214

页数：7

共 74 条

[1] Triazolopyridines 20. Hydrogenation reactions [J].

Abarca, B ;

Ballesteros, R ;

Elmasnouy, M .

TETRAHEDRON, 1999, 55 (44) :12881-12884

[2] Active nickel-based reduction of organic compounds [J].

Alonso, F ;

Radivoy, G ;

Yus, M .

RUSSIAN CHEMICAL BULLETIN, 2003, 52 (12) :2563-2576

[3] Hydrodehalogenation of organic halides using the CuCl2.2H2O-Li-arene(cat.) combination [J].

Alonso, F ;

Moglie, Y ;

Radivoy, G ;

Vitale, C ;

Yus, M .

APPLIED CATALYSIS A-GENERAL, 2004, 271 (1-2) :171-176

[4] The NiCl2-Li-arene(cat.) combination: A versatile reducing mixture [J].

Alonso, F ;

Yus, M .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (05) :284-293

[5]

Alonso F, 2003, SYNTHESIS-STUTTGART, P443

[6] New synthetic methodologies based on active transition metals [J].

Alonso, Francisco ;

Yust, Miguel .

PURE AND APPLIED CHEMISTRY, 2008, 80 (05) :1005-1012

[7] Unsupported Copper Nanoparticles in the 1,3-Dipolar Cycloaddition of Terminal Alkynes and Azides [J].

Alonso, Francisco ;

Moglie, Yanina ;

Radivoy, Gabriel ;

Yus, Miguel .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (10) :1875-1884

[8] Copper nanoparticles in click chemistry: an alternative catalytic system for the cycloaddition of terminal alkynes and azides [J].

Alonso, Francisco ;

Moglie, Yanina ;

Radivoy, Gabriel ;

Yus, Miguel .

TETRAHEDRON LETTERS, 2009, 50 (20) :2358-2362

[9]

Anderson J.A., 2005, SUPPORTED METALS CAT

[10] 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

← 1 2 3 4 5 6 7 8 →