Pd nanoparticles supported on Fe 3 O 4 @SiO 2 -Schiff base as an efficient magnetically recoverable nanocatalyst for Suz
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Pd nanoparticles supported on Fe3O4@SiO2‑Schiff base as an efficient magnetically recoverable nanocatalyst for Suzuki–Miyaura coupling reaction Najmeh Amirmahani1,2 · Nosrat O. Mahmoodi3 · Mohammad Malakootian2 · Abbas Pardakhty4 · Neda Seyedi5 Received: 19 May 2020 / Accepted: 21 July 2020 © Springer Nature B.V. 2020
Abstract In this work, Pd nanoparticles (Pd-NPs) were decorated on modified magnetic nanoparticles (MNPs) and used as an efficient and recyclable catalyst for the Suzuki cross-coupling reaction of aryl halides with phenylboronic acid (PhB(OH)2) in a green solvent. The prepared nanocomposite was characterized by field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy, transmission electron microscopy, Fourier transforms infrared spectroscopy, X-ray powder diffraction, thermogravimetric analysis/differential thermal analysis, and vibrating sample magnetometry. All analyses confirmed the successful modification of MNPs and immobilization of Pd on modified MNPs. This catalyst exhibited superior catalytic activity and stability in the suzuki cross-coupling reaction of PhB(OH)2 and aryl halide derivatives. This protocol includes some advantages, such as magnetically reusability of the catalyst, mild experimental conditions, green solvent, excellent yields of the product (52–98%), and short reaction times (4–33 min). The catalyst could be reused for six successive runs without any significant loss of its efficiency.
* Nosrat O. Mahmoodi [email protected]; [email protected] 1
Department of Chemistry, University Campus 2, University of Guilan, PO Box 41335‑1914, Rasht, Iran
2
Environmental Health Engineering Research Center, Kerman University of Medical Sciences, PO Box 76175‑531, Kerman, Iran
3
Department of Organic Chemistry, Faculty of Sciences, University of Guilan, PO Box 41335‑1914, Rasht, Iran
4
Pharmaceutics Research Center, Neuropharmacology Institute, Kerman University of Medical Sciences, PO Box 76175‑531, Kerman, Iran
5
Department of Chemistry, Faculty of Science, University of Jiroft, Jiroft, Iran
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Graphic abstract
X
HO
K2CO3 H2O:EtOH 75 oC
B
OH
R
SiO2
O O
Fe3O4
Si
O O O O
Si
N (CH2)3 (CH2)3 N
O
Pd O
R
R = H, 4-OMe, 4-NO2, 2-OMe,-NO2, 3NO2, 3-Me, 4-Me, X = Br, I
Keywords Magnetite nanoparticles · Nanocomposites · Suzuki–Miyaura coupling reaction · C–C coupling
Introduction The formation of Ar–Ar bonds has major importance in various fields of organic and medicinal chemistry. Biaryl compounds are useful frameworks for various polymers, agrochemicals, pharmaceuticals, and natural products including flavonoids, terpenes, alkaloids, tannins, peptides, and glycopeptides [1, 2]. The classical methods for the synthesis of biaryls are the Ullmann reaction [3, 4], Gomberg-Bachmann-Hey reaction [5], Pschorr cyclization [6], and Gatterman synthesis [7]. Among these reported methods for the C–C coupling in organic reaction, transition-metal-catalyzed reaction, particularly, Pd-catalyzed, has b
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