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Dendrimer‐encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe 3 O 4 @SiO 2 nanoparticles as a novel recyclable catalyst for N ‐arylation of nitrogen heterocycles and green synthesis of 5‐substituted 1 H ‐tetrazoles
Author(s) -
Esmaeilpour Mohsen,
Sardarian Ali Reza,
Firouzabadi Habib
Publication year - 2018
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.4300
Subject(s) - thermogravimetric analysis , superparamagnetism , catalysis , chemistry , nanoparticle , fourier transform infrared spectroscopy , magnetic nanoparticles , nuclear chemistry , dendrimer , dynamic light scattering , inductively coupled plasma , chemical engineering , analytical chemistry (journal) , magnetization , polymer chemistry , nanotechnology , organic chemistry , materials science , physics , quantum mechanics , magnetic field , engineering , plasma
In this study, dendrimer‐encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe 3 O 4 @SiO 2 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 50 nm. Also, the amount of Cu is determined to be 0.51 mmol/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 1 H ‐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.