Dendrimer-encapsulated Cu() nanoparticles immobilized on superparamagnetic Fe3O4@SiO2 nanoparticles as a novel recyclable catalyst for N-arylation of nitrogen heterocycles and green synthesis of 5-substituted 1H-tetrazoles

被引:59
作者
Esmaeilpour, Mohsen [1 ]
Sardarian, Ali Reza [1 ]
Firouzabadi, Habib [1 ]
机构
[1] Shiraz Univ, Dept Chem, Coll Sci, Shiraz 7194684795, Iran
关键词
Dendrimer-encapsulated Cu(); 5-substituted; 1H-tetrazoles; green synthesis; magnetic nanoparticles; N-arylation; ARYL HALIDES; BOND FORMATION; HETEROGENEOUS CATALYSTS; EFFICIENT CATALYST; ARYLBORONIC ACIDS; REUSABLE CATALYST; 3+2 CYCLOADDITION; TRIMETHYLSILYL AZIDE; MILD CONDITIONS; SUZUKI-MIYAURA;
D O I
10.1002/aoc.4300
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In this study, dendrimer-encapsulated Cu() nanoparticles immobilized on superparamagnetic Fe3O4@SiO2 nanoparticles were prepared via a multistep-synthesis. Then, the synthesized composite was fully characterized by various techniques such as fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), dynamic light scattering (DLS), UV-vis spectroscopy, energy dispersive X-ray analysis (EDX), thermogravimetric analysis (TGA) and vibration sample magnetometer (VSM). From the information gained by FE-SEM and TEM studies it can be inferred that the particles are mostly spherical in shape and have an average size of 50nm. Also, the amount of Cu is determined to be 0.51mmol/g in the catalyst by inductively coupled plasma (ICP) analyzer. This magnetic nano-compound has been successfully applied as a highly efficient, magnetically recoverable and stable catalyst for N-arylation of nitrogen heterocycles with aryl halides (I, Br) and arylboronic acids without using external ligands or additives. The catalyst was also employed in a one-pot, three-component reaction for the efficient and green synthesis of 5-substituted 1H-tetrazoles using various aldehydes, hydroxylamine hydrochloride and sodium azide in water. The magnetic catalyst can be easily separated by an external magnet bar and is recycled seven times without significant loss of its activity.
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页数:16
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共 77 条
[1]   Separable catalysts in one-pot syntheses for greener chemistry [J].
Abu-Reziq, Raed ;
Wang, Dashan ;
Post, Michael ;
Alper, Howard .
CHEMISTRY OF MATERIALS, 2008, 20 (07) :2544-2550
[2]   Dendrimers Designed for Functions: From Physical, Photophysical, and Supramolecular Properties to Applications in Sensing, Catalysis, Molecular Electronics, Photonics, and Nanomedicine [J].
Astruc, Didier ;
Boisselier, Elodie ;
Ornelas, Catia .
CHEMICAL REVIEWS, 2010, 110 (04) :1857-1959
[3]   Structure-Activity Study of Pentamidine Analogues as Antiprotozoal Agents [J].
Bakunova, Svetlana M. ;
Bakunov, Stanislav A. ;
Patrick, Donald A. ;
Kumar, E. V. K. Suresh ;
Ohemeng, Kwasi A. ;
Bridges, Arlene S. ;
Wenzler, Tanja ;
Barszcz, Todd ;
Jones, Susan Kilgore ;
Werbovetz, Karl A. ;
Brun, Reto ;
Tidwell, Richard R. .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (07) :2016-2035
[4]  
Butler R.N., 1996, Comprehensive Heterocyclic Chemistry II
[5]   Synthesis of 1-aryl indoles via coupling reaction of indoles and aryl halides catalyzed by CuI/metformin [J].
Chen, Hu ;
Lei, Min ;
Hu, Lihong .
TETRAHEDRON, 2014, 70 (35) :5626-5631
[6]  
Chouhan G., 2007, CHEM COMMUN, P4809
[7]   Mild conditions for copper-catalysed N-arylation of pyrazoles [J].
Cristau, HJ ;
Cellier, PP ;
Spindler, JF ;
Taillefer, M .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (04) :695-709
[8]   Gold nanoparticles: Assembly, supramolecular chemistry, quantum-size-related properties, and applications toward biology, catalysis, and nanotechnology [J].
Daniel, MC ;
Astruc, D .
CHEMICAL REVIEWS, 2004, 104 (01) :293-346
[9]   Salen complex of Cu(II) supported on superparamagnetic Fe3O4@SiO2 nanoparticles: An efficient and recyclable catalyst for synthesis of 1-and 5-substituted 1H-tetrazoles [J].
Dehghani, Farzaneh ;
Sardarian, Ali Reza ;
Esmaeilpour, Mohsen .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 743 :87-96
[10]   A green one-pot three-component synthesis of spirooxindoles under conventional heating conditions or microwave irradiation by using Fe3O4@SiO2-imid-PMAn magnetic porous nanospheres as a recyclable catalyst [J].
Esmaeilpour, Mohsen ;
Javidi, Jaber ;
Divar, Masoumeh .
JOURNAL OF MAGNETISM AND MAGNETIC MATERIALS, 2017, 423 :232-240