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Pd(0) complex of fuberidazole modified magnetic nanoparticles: A novel magnetically retrievable high‐performance catalyst for Suzuki and Stille C‐C coupling reactions
Author(s) -
Nouri Kheirollah,
Ghassemzadeh Mitra,
Mohsenzadeh Farshid,
Afsharpour Maryam
Publication year - 2020
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.5771
Subject(s) - chemistry , stille reaction , aryl , catalysis , coupling reaction , iodide , palladium , nuclear chemistry , bromide , leaching (pedology) , suzuki reaction , heterogeneous catalysis , nanoparticle , inorganic chemistry , organic chemistry , chemical engineering , alkyl , environmental science , soil science , soil water , engineering
Fuberidazole has been successfully immobilized onto nano‐Fe 3 O 4 supported (3‐chloropropyl)trimethoxysilane (3‐CPTS) leading to a novel functionalized magnetic nanoparticle (FB/MNP). The Pd(0) complex, Pd‐FB/MNP, was prepared by grafting Pd (OAc) 2 on FB/MNP and subsequent reduction of a synthesized Pd (II) complex using NaBH 4 . Pd‐FB/MNP has been characterized by FT‐IR, SEM, TGA, XRD, ICP, EDS, BET and VSM. The Pd(0) complex proved to be an efficient phosphine‐ and halide‐free recyclable heterogeneous catalyst for Suzuki as well as for Stille C‐C coupling reactions showing high catalytic activity (up to 98%). Its catalytic activity in both reactions has been studied in PEG‐400 as a green solvent. Besides, the selectivity of aryl iodide and aryl bromide over aryl chloride is observed during the C‐C coupling reaction. The catalyst could be recovered easily from the reaction mixture using an external magnet device and recycled several times without considerable loss in activity. Additionally, the results of a palladium leaching test of the nano‐catalyst demonstrate that no leaching of Pd took place during the C‐C coupling process making the procedure environmentally friendly.