Copper nanoparticles supported on CeO2 as an efficient catalyst for click reactions of azides with alkynes

被引:34
作者
Amini, Mojtaba [1 ]
Hassandoost, Ramin [1 ]
Bagherzadeh, Mojtaba [2 ]
Gautam, Sanjeev [3 ]
Chae, Keun Hwa [4 ]
机构
[1] Univ Maragheh, Dept Chem, Fac Sci, Maragheh, Iran
[2] Sharif Univ Technol, Dept Chem, POB 11155-3615, Tehran, Iran
[3] Panjab Univ, Univ Inst Chem Engn & Technol SSB UICET, Chandigarh 160014, India
[4] Korea Inst Sci & Technol, Adv Anal Ctr, Seoul 136791, South Korea
关键词
Nanoparticles; Copper; CeO2; 1,3-dipolar cycloaddition; HETEROGENEOUS CATALYST; 3+2 CYCLOADDITION; CHEMISTRY; 1,2,3-TRIAZOLES; COMPLEXES;
D O I
10.1016/j.catcom.2016.07.006
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Readily prepared copper nanoparticles supported on CeO2 have been found to effectively catalyse the 1,3-dipolar cycloaddition (CuAAC) of a variety terminal alkynes and organic azides generated in situ from sodium azide and different organic halides furnishing the corresponding 1,2,3-triazoles in excellent yields. Cu nanoparticles supported on CeO2 have been characterized by X-ray diffraction analysis, energy dispersive X-ray analysis, scanning electron microscope and transmission electron microscope. The salient features of the present protocol are shorter reaction time, mild reaction conditions, reusability of the catalyst, and applicability to a wide range of substrates. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码:13 / 16
页数:4
相关论文
共 36 条
[1]   Cube-octameric silsesquioxane-mediated cargo copper Schiff base for efficient click reaction in aqueous media [J].
Akbari, Ali ;
Arsalani, Nasser ;
Amini, Mojtaba ;
Jabbari, Esmaiel .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2016, 414 :47-54
[2]   Copper Nanoparticles in Click Chemistry [J].
Alonso, Francisco ;
Moglie, Yanina ;
Radivoy, Gabriel .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (09) :2516-2528
[3]   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
[4]   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
[5]   Synthesis, structure, and catalytic properties of copper, palladium and cobalt complexes containing an N,O-type bidentate thiazoline ligand [J].
Amini, Mojtaba ;
Bayrami, Arshad ;
Marashi, Mohammad Nazari ;
Arab, Ali ;
Ellern, Arkady ;
Woo, L. Keith .
INORGANICA CHIMICA ACTA, 2016, 443 :22-27
[6]   Rapid oxidative degradation of methylene blue by various metal oxides doped with vanadium [J].
Amini, Mojtaba ;
Ashrafi, Mahdi ;
Gautam, Sanjeev ;
Chae, Keun Hwa .
RSC ADVANCES, 2015, 5 (47) :37469-37475
[7]   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
[8]   Click chemistry in CuI-zeolites:: The Huisgen [3+2]-cycloaddition [J].
Chassaing, Stefan ;
Kumarraja, Mayilvasagam ;
Sido, Abdelkarim Sani Souna ;
Pale, Patrick ;
Sommer, Jean .
ORGANIC LETTERS, 2007, 9 (05) :883-886
[9]   [(NHC)2Cu]X Complexes as Efficient Catalysts for Azide-Alkyne Click Chemistry at Low Catalyst Loadings [J].
Diez-Gonzalez, Silvia ;
Nolan, Steven P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (46) :8881-8884
[10]   A [(NHC)CuCl] complex as a latent Click catalyst [J].
Diez-Gonzalez, Silvia ;
Stevens, Edwin D. ;
Nolan, Steven P. .
CHEMICAL COMMUNICATIONS, 2008, (39) :4747-4749