C-N Bond Formation Using Highly Effective and Reusable Nickel Ferrite Nanoparticles in Water

被引:27
作者
Moghaddam, Firouz Matloubi [1 ]
Tavakoli, Ghazal [1 ]
Moafi, Atiyeh [1 ]
Saberi, Vahid [1 ]
Rezvani, Hamid Reza [1 ]
机构
[1] Sharif Univ Technol, Lab Organ Synth & Nat Prod, Dept Chem, Tehran, Iran
关键词
amination; heterogeneous catalysis; iron; nanoparticles; nickel; COPPER-CATALYZED AMINATION; CROSS-COUPLING REACTIONS; MAGNETIC NANOPARTICLES; REDUCTIVE AMINATION; ARYL HALIDES; ORTHOPALLADATED COMPLEX; CUFE2O4; NANOPARTICLES; SUPPORTED PALLADIUM; EFFICIENT; AMINES;
D O I
10.1002/cctc.201402556
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
Nickel ferrite nanoparticles were used as a catalyst system for C-N bond formation in water under conventional heating conditions. These nanoparticles were synthesized by using the co-precipitation method and were analyzed by using TEM, SEM, XRD, X-ray fluorescence, and FTIR techniques. The magnetization behavior of nanoparticles was also investigated by measuring the hysteresis curve of the sample, which confirmed the (s)uperparamagnetic nature of the catalyst. By using this catalyst system, various types of amines and amides, including primary and secondary ones, can react with different types of aryl halides. In addition, it is a recyclable and reusable catalyst system with high turnover efficiency. The reactions proceed in water as a green solvent, which result in good to excellent yields in short times.
引用
收藏
页码:3474 / 3481
页数:8
相关论文
共 68 条
[11]   Pd-Catalyzed Cross-Coupling Reactions of Amides and Aryl Mesylates [J].
Dooleweerdt, Karin ;
Fors, Brett P. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2010, 12 (10) :2350-2353
[12]  
Eller K., 2000, ULLMANNS ENCY IND CH
[13]   Easy access to novel substituted 6-aminoimidazo[1,2-a]pyridines using palladium- and copper-catalyzed aminations [J].
Enguehard, C ;
Allouchi, H ;
Gueiffier, A ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4367-4370
[14]   Palladium nanoparticles supported on agarose-functionalized magnetic nanoparticles of Fe3O4 as a recyclable catalyst for C-C bond formation via Suzuki-Miyaura, Heck-Mizoroki and Sonogashira-Hagihara coupling reactions [J].
Firouzabadi, Habib ;
Iranpoor, Nasser ;
Gholinejad, Mohammad ;
Akbari, Samira ;
Jeddi, Neda .
RSC ADVANCES, 2014, 4 (33) :17060-17070
[15]   Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds [J].
Fischer, Carolin ;
Koenig, Burkhard .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :59-74
[16]   Unsymmetrical ureas. Synthetic methodologies and application in drug design [J].
Gallou, Isabelle .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2007, 39 (04) :355-383
[17]   GABRIEL SYNTHESIS OF PRIMARY AMINES [J].
GIBSON, MS ;
BRADSHAW, RW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (12) :919-&
[18]   Concerning phenylization in the presence of copper as a catalytic agent. [J].
Goldberg, I .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1906, 39 :1691-1692
[19]  
Gomez S, 2002, ADV SYNTH CATAL, V344, P1037, DOI 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO
[20]  
2-3