Highly Active Fe3O4@SBA-15@NHC-Pd Catalyst for Suzuki–Miyaura Cross-Coupling Reaction

A novel Pd-NHC functionalized magnetic Fe 3 O 4 @SBA-15@NHC-Pd was synthesized and used as an efficient heterogeneous catalyst in the Suzuki–Miyaura C–C bond formation reactions. The Fe 3 O 4 @SBA-15@NHC-Pd characterized by X-Ray Diffraction (XRD), X-ray Photoelectron Spectroscopy (XPS), Fourier Tra...

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Bibliographic Details
Published in:Catalysis letters 2022-06, Vol.152 (6), p.1621-1638
Main Authors: Akkoç, Mitat, Buğday, Nesrin, Altın, Serdar, Özdemir, İsmail, Yaşar, Sedat
Format: Article
Language:English
Subjects:
Aqueous solutions
Aromatic compounds
Bromides
Catalysis
Catalysts
Chemical reactions
Chemistry
Chemistry and Materials Science
Covalent bonds
Cross coupling
Differential thermal analysis
Differential thermogravimetric analysis
Emission analysis
Energy dispersive X ray analysis
Fourier transforms
Inductively coupled plasma
Industrial Chemistry/Chemical Engineering
Infrared spectroscopy
Iron oxides
Microscopy
Nanoparticles
Optical emission spectroscopy
Organometallic Chemistry
Palladium
Photoelectrons
Physical Chemistry
Potassium carbonate
Reducing agents
Room temperature
Spectrum analysis
Transmission electron microscopy
X ray analysis
X ray photoelectron spectroscopy
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Summary:A novel Pd-NHC functionalized magnetic Fe 3 O 4 @SBA-15@NHC-Pd was synthesized and used as an efficient heterogeneous catalyst in the Suzuki–Miyaura C–C bond formation reactions. The Fe 3 O 4 @SBA-15@NHC-Pd characterized by X-Ray Diffraction (XRD), X-ray Photoelectron Spectroscopy (XPS), Fourier Transform Infrared (FTIR) spectroscopy, Scanning Electron Microscopy (SEM), Transmission Electron Microscopy (TEM), Energy Dispersive X-ray analysis (EDX), Thermogravimetric Analysis (TGA), Differential Thermal Analysis (DTA). The Inductively Coupled Plasma-Optical emission spectroscopy (ICP-OES) analysis was used to determine the exact amount of Pd (0.33 wt%) in Fe 3 O 4 @SBA-15@NHC-Pd. The TEM images of the catalyst showed the existence of palladium nanoparticles immobilized in the catalyst's structure, while no reducing agent was used. The NHC moieties in the catalyst structure could be stabilize Pd(0) nanoparticles prevents agglomeration. The magnetic catalyst was effectively used in the Suzuki–Miyaura cross-coupling reaction of substituted phenylboronic acid derivatives with (hetero)aryl bromides in the presence of a K 2 CO 3 at room temperature in aqueous media and magnetic catalyst could be simply extracted from the reaction mixture by an external magnet. Different aryl bromides were converted to coupled-products in excellent yields with spectacular TOFs values (up to 1,960,339 h −1 ); in the presence of 1 mg of Fe 3 O 4 @SBA-15@NHC-Pd catalyst (contains 3.1 × 10 –6  mol% Pd) at room temperature in aqueous media. After reusability experiments, it is found that this catalyst was effectively used up to ten times in the reaction with almost consistent catalytic efficiency. A decrease in the activity of the 10th reused catalyst was found as 9%. Graphic Abstract
ISSN:1011-372X
1572-879X
DOI:10.1007/s10562-021-03755-w