Copper Aluminate Spinel in Click Chemistry: An Efficient Heterogeneous Nanocatalyst for the Highly Regioselective Synthesis of Triazoles in Water

被引:21
作者
Khalili, Dariush [1 ]
Kavoosi, Leila [1 ]
Khalafi-Nezhad, Ali [1 ]
机构
[1] Shiraz Univ, Dept Chem, Coll Sci, Shiraz 71454, Iran
关键词
click chemistry; copper catalysis; triazoles; epoxides; azides; alkynes; CYCLOADDITION; CATALYST; LIGAND; CUAAC; CU; 1,2,3-TRIAZOLES; NANOPARTICLES; DERIVATIVES; CUAL2O4; IODIDE;
D O I
10.1055/s-0039-1690719
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An expeditious protocol for the one-pot synthesis of 1,4-disubstituted (beta-hydroxy)-1,2,3-triazoles in an aqueous medium has been developed using copper aluminate nanoparticles. This heterogeneous catalytic system was found to drive a multicomponent click reaction between organic azides (generated in situ from epoxides or halides) and terminal aliphatic or aromatic alkynes in up to 96% yield without the need for a reducing agent. Structurally diverse 1,2,3-triazoles were synthesized in good to excellent yields, and the catalyst could be easily separated by simple filtration, recycled, and reused in six subsequent cycles.
引用
收藏
页码:2136 / 2142
页数:7
相关论文
共 55 条
[1]   Sustainable Construction of Heterocyclic 1,2,3-Triazoles by Strict Click [3+2] Cycloaddition Reactions Between Azides and Alkynes on Copper/Carbon in Water [J].
Aflak, Noura ;
Ben El Ayouchia, Hicham ;
Bahsis, Lahoucine ;
El Mouchtari, El Mountassir ;
Julve, Miguel ;
Rafqah, Salah ;
Anane, Hafid ;
Stiriba, Salah-Eddine .
FRONTIERS IN CHEMISTRY, 2019, 7
[2]   Alumina-Supported Copper Iodide: An Efficient and Recyclable Catalyst for Microwave-Assisted Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via Three-Component Reaction in Water [J].
Agalave, Sandip G. ;
Pharande, Shrikant G. ;
Gade, Swapna M. ;
Pore, Vandana S. .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (09) :943-951
[3]   Design, click synthesis, anticancer screening and docking studies of novel benzothiazole-1,2,3-triazoles appended with some bioactive benzofused heterocycles [J].
Aouad, Mohamed Reda ;
Almehmadi, Meshal A. ;
Rezki, Nadjet ;
Al-blewi, Fawzia Faleh ;
Messali, Mouslim ;
Ali, Imran .
JOURNAL OF MOLECULAR STRUCTURE, 2019, 1188 :153-164
[4]   Linear and Convergent Syntheses of Bifunctional Hydroxy-Bisphosphonic Compounds as Potential Bone-Targeting Prodrugs [J].
Aoun, Sameh ;
Sierocki, Pierre ;
Lebreton, Jacques ;
Mathe-Allainmat, Monique .
SYNTHESIS-STUTTGART, 2019, 51 (18) :3556-3566
[5]   A reusable polymer-supported copper(I) catalyst for triazole click reaction on water: An experimental and computational study [J].
Bahsis, Lahoucine ;
Ben El Ayouchia, Hicham ;
Anane, Hafid ;
Pascual-Alvarez, Alejandro ;
De Munno, Giovanni ;
Julve, Miguel ;
Stiriba, Salah-Eddine .
APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (04)
[6]   CuO-CuAl2O4 and D-glucose catalyzed synthesis of a family of excited state intramolecular proton transfer imidazo[1,2-a]pyridine analogues and their optical properties [J].
Balijapalli, Umamahesh ;
Iyer, Sathiyanarayanan Kulathu .
DYES AND PIGMENTS, 2015, 121 :88-98
[7]   CuAAC: An Efficient Click Chemistry Reaction on Solid Phase [J].
Castro, Vida ;
Rodriguez, Hortensia ;
Abericio, Fernando .
ACS COMBINATORIAL SCIENCE, 2016, 18 (01) :1-14
[8]   When CuAAC 'Click Chemistry' goes heterogeneous [J].
Chassaing, S. ;
Beneteau, V. ;
Pale, P. .
CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (04) :923-957
[9]   Click Chemistry in zeolites: Copper(I) zeolites as new heterogeneous and ligand-free catalysts for the Huisgen [3+2] cycloaddition [J].
Chassaing, Stefan ;
Sido, Abdelkarim Sani Souna ;
Alix, Aurelien ;
Kumarraja, Mayilvasagam ;
Pale, Patrick ;
Sommer, Jean .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (22) :6713-6721
[10]   Microwave-mediated synthesis of spinel CuAl2O4 nanocomposites for enhanced electrochemical and catalytic performance [J].
Chaudhary, Ratiram Gomaji ;
Sonkusare, Vaishali N. ;
Bhusari, Ganesh S. ;
Mondal, Aniruddha ;
Shaik, Dadamia P. M. D. ;
Juneja, Harjeet D. .
RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (03) :2039-2060