Pd based on 2-Aminopyrimidine and 1H-benzo[d]imidazol-2-amine functionalizedFe3O4 nanoparticles as novel recyclable magnetic nanocatalysts for Ullmann coupling reaction

被引:17
作者
Chen, Jin [1 ]
Dai, Linfang [1 ]
Li, Jiayu [1 ]
Mohammadnia, Majid [2 ]
机构
[1] Cent South Univ, Sch Business, Changsha 410000, Hunan, Peoples R China
[2] Islamic Azad Univ, Young Researcher & Elite Club, Dept Chem, Bojnord Branch, Bojnourd, Iran
关键词
1H-benzo[d ]imidazol-2-amine; 2-Aminopyrimidine; magnetic; Nanocatalyst; palladium nanoparticles; O BOND FORMATION; C-O; FE3O4; NANOPARTICLES; EFFICIENT CATALYST; DIARYL ETHERS; PALLADIUM NANOPARTICLES; CELLULOSE NANOCRYSTALS; GREEN SYNTHESIS; ARYL HALIDES; SOLID BASE;
D O I
10.1002/aoc.5708
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In this study, Pd based on 2-Aminopyrimidine and 1H-benzo[d]imidazol-2-amine functionalized Fe3O4 magnetic nanoparticles [(Pd-APM-PSi-Fe3O4) and (Pd-BIA-PSi-Fe3O4)] was designed and used for the synthesis of di aryl ether by Ulmann cross-coupling reactions. Ulmann reaction performed with mixing of the arylhalides and phenol derivatives in DMF solvent. The prepared catalysts were characterized with various analytical techniques such as FT-IR, XRD, TGA, SEM, TEM, EDX, ICP and VSM. Pd-APM-PSi-Fe3O4 and Pd-BIA-PSi-Fe3O4 catalysts demonstrated good to excellent yields catalytic efficiency for Ulmann reactions in comparison with to commercial palladium catalysts. The catalyst is easily recycled and reused without loss of the catalytic activity. The combined merits of reusable catalyst conditions make the condensation with safe operation, no leaching of pd into environment, low pollution, rapid access to products and simple workup. Also, these novel magnetic nanocatalysts are superior to the industry standard Pd in every relevant aspect. They feature a way higher initial activity, a much more convenient separation, better recycling, and less contamination of the products. Last but not least, they can be very easily prepared from commercially available Fe3O4 nanoparticles using standard laboratory equipment.
引用
收藏
页数:15
相关论文
共 47 条
[21]   Potassium tert-butoxide-mediated synthesis of unsymmetrical diaryl ethers, sulfides and selenides from aryl bromides [J].
Kumar, Amit ;
Bhakuni, Bhagat Singh ;
Prasad, Ch. Durga ;
Kumar, Shailesh ;
Kumar, Sangit .
TETRAHEDRON, 2013, 69 (26) :5383-5392
[22]   Effects of single- and multi-organic acid ligands on adsorption of copper by Fe3O4/graphene oxide-supported DCTA [J].
Liu, Shaobo ;
Wang, Hui ;
Chai, Liyuan ;
Li, Meifang .
JOURNAL OF COLLOID AND INTERFACE SCIENCE, 2016, 478 :288-295
[23]  
Mirzajani R, 2015, J IND ENG CHEM, V23, P171
[24]   Barberry fruit extract assisted in situ green synthesis of Cu nanoparticles supported on a reduced graphene oxide-Fe3O4 nanocomposite as a magnetically separable and reusable catalyst for the O-arylation of phenols with aryl halides under ligand-free conditions [J].
Nasrollahzadeh, Mahmoud ;
Maham, Mehdi ;
Rostami-Vartooni, Akbar ;
Bagherzadeh, Mojtaba ;
Sajadi, S. Mohammad .
RSC ADVANCES, 2015, 5 (79) :64769-64780
[25]   An efficient Ullmann-type C-O bond formation catalyzed by an air-stable copper(I)-bipyridyl complex [J].
Niu, Jiajia ;
Zhou, Hua ;
Li, Zhigang ;
Xu, Jingwei ;
Hu, Shaojing .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) :7814-7817
[26]  
Qafisheh N, 2002, ADV SYNTH CATAL, V344, P1079, DOI 10.1002/1615-4169(200212)344:10<1079::AID-ADSC1079>3.0.CO
[27]  
2-K
[28]   2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide as a novel ligand for the copper-catalyzed coupling reaction of phenols and aryl halides [J].
Qiu, Yatao ;
Jia, Weijun ;
Yao, Zhiyi ;
Wu, Fanhong ;
Jiang, Sheng .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (09) :1502-1510
[29]   Immobilization of a novel cold active esterase onto Fe3O4∼cellulose nano-composite enhances catalytic properties [J].
Rahman, Mohammad Asadur ;
Culsum, Umma ;
Kumar, Ashok ;
Gao, Haofeng ;
Hu, Nan .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2016, 87 :488-497
[30]   Production of cellulose nanocrystals using hydrobromic acid and click reactions on their surface [J].
Sadeghifar, Hasan ;
Filpponen, Ilari ;
Clarke, Sarah P. ;
Brougham, Dermot F. ;
Argyropoulos, Dimitris S. .
JOURNAL OF MATERIALS SCIENCE, 2011, 46 (22) :7344-7355