Cuprous oxide on charcoal-catalyzed ligand-free synthesis of 1,4-disubstituted 1,2,3-triazoles via click chemistry

被引：38

作者：

Lopez-Ruiz, Heraclio ^{[1
]}

Emilio de la Cerda-Pedro, Jose ^{[1
]}

Rojas-Lima, Susana ^{[1
]}

Perez-Perez, Imelda ^{[1
]}

Viridiana Rodriguez-Sanchez, Brianda ^{[1
]}

Santillan, Rosa ^{[2
]}

Coreno, Oscar ^{[3
]}

机构：

[1] Univ Autonoma Estado Hidalgo, Area Acad Quim, Carretera Pachuca Tulancingo Km 4-5,Ciudad Univ, Mineral De La Reforma 42184, Hidalgo, Mexico

[2] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico

[3] Univ Guanajuato, Dept Ingn Civil, Guanajuato 36000, Mexico

来源：

ARKIVOC | 2013年

关键词：

1,3-Dipolar cycloaddition; click chemistry; Cu2O/C; triazoles; ONE-POT SYNTHESIS; CU-I-ZEOLITES; COPPER NANOPARTICLES; TERMINAL ALKYNES; 1,3-DIPOLAR CYCLOADDITION; HETEROGENEOUS CATALYST; HUISGEN CYCLOADDITION; ORGANIC AZIDES; EFFICIENT; WATER;

D O I：

10.3998/ark.5550190.0014.312

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cuprous oxide on charcoal (Cu2O/C), the preparation of which is described for the first time, catalyzes the formation of 1,4-disubstituted 1,2,3-triazoles from organic azides and terminal alkynes in good to excellent yields (69-94%). These disubstituted triazoles can be equally efficiently generated in a one-pot process from alkyl bromides, sodium azide, and terminal acetylenes in 50% aqueous isopropanol containing a suspension of the catalyst. This obviates the necessity to isolate potentially explosive organic azides.

引用

页码：139 / 164

页数：26

共 67 条

[1] 'Click chemistry' in CuI-zeolites:: a convenient access to glycoconjugates [J].

Alix, Aurlien ;

Chassaing, Stefan ;

Pale, Patrick ;

Sommer, Jean .

TETRAHEDRON, 2008, 64 (37) :8922-8929

[2] Click chemistry from organic halides, diazonium salts and anilines in water catalysed by copper nanoparticles on activated carbon [J].

Alonso, Francisco ;

Moglie, Yanina ;

Radivoy, Gabriel ;

Yus, Miguel .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (18) :6385-6395

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

Alonso, Francisco ;

Moglie, Yanina ;

Radivoy, Gabriel ;

Yus, Miguel .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) :3208-3214

[4] 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

[5] 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

[6]

[Anonymous], 1984, 1 3 DIPOLAR CYCLOADD

[7] Zeo-click synthesis: CuI-zeolite-catalyzed one-pot two-step synthesis of triazoles from halides and related compounds [J].

Beneteau, Valerie ;

Olmos, Andrea ;

Boningari, Thirupathi ;

Sommer, Jean ;

Pale, Patrick .

TETRAHEDRON LETTERS, 2010, 51 (28) :3673-3677

[8] 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

[9] Study of copper(I) catalysts for the synthesis of carbanucleosides via azide-alkyne 1,3-dipolar cycloaddition [J].

Broggi, Julie ;

Diez-Gonzalez, Silvia ;

Petersen, Jeffrey L. ;

Berteina-Raboin, Sabine ;

Nolan, Steven P. ;

Agrofoglio, Luigi A. .

SYNTHESIS-STUTTGART, 2008, (01) :141-148

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

Chan, TR ;

Hilgraf, R ;

Sharpless, KB ;

Fokin, VV .

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

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