Hydrothermal Synthesis of CuFe2O4 Magnetic Nanoparticles as Active and Robust Catalyst for N-arylation of Indole and Imidazole with Aryl Halide

被引:38
作者
Nakhate, Akhil V. [1 ]
Yadav, Ganapati D. [1 ]
机构
[1] Inst Chem Technol, Dept Chem Engn, Nathalal Parekh Marg, Bombay 400019, Maharashtra, India
关键词
Hydrothermal synthesis; Heterogeneous catalyst; Magnetic separation; N-arylation; Spinel ferrite nanospheres; CROSS-COUPLING REACTIONS; GRAPHENE OXIDE MONOLITH; C-N; SUPERPARAMAGNETIC NANOPARTICLES; ANTIPSYCHOTIC SERTINDOLE; FERRITE NANOPARTICLES; RECYCLABLE CATALYST; HIGHLY EFFICIENT; PARTIAL AGONISTS; RECEPTOR;
D O I
10.1002/slct.201601846
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Spinel ferrite magnetic nanoparticles are superior to the conventional catalysts. Here we report the synthesis of different types of spinel ferrite nanoparticles, MFe2O4 (M= Cu, Mn, Mg, Co, Ni), by a hydrothermal method. The prepared spinel ferrite nanoparticles were used for the N-arylation reaction of indole with iodobenzene. Among these CuFe2O4 nanoparticles exhibited the best activity and selectivity for N-arylation under ligand free condition. The prepared spinel ferrite microspheres were well characterised by using various characterization techniques such as TEM, XRD, XPS, SEM, EDXA, FT-IR, N-2 adsorption desorption measurements and TGA. The effect of various parameters were studied such as solvent, base, speed of agitation, mole ratio, catalyst loading and temperature in the reaction of indole with iodobenzene. Best conversion and yield were achieved at 110 degrees C and 1x10(-3) g/cm(3) catalyst loading. Notably, CuFe2O4 magnetic nanoparticles were completely recovered and could be reused six times without any noticeable loss of activity. Reaction mechanism and kinetics are also presented.
引用
收藏
页码:2395 / 2405
页数:11
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[1]   Serotonin 5-HT2 receptor, dopamine D-2 receptor, and alpha(1) adrenoceptor antagonists. Conformationally flexible analogues of the atypical antipsychotic sertindole [J].
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