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

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Abstract

A novel Pd-NHC functionalized magnetic Fe3O4@SBA-15@NHC-Pd was synthesized and used as an efficient heterogeneous catalyst in the Suzuki–Miyaura C–C bond formation reactions. The Fe3O4@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 Fe3O4@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 K2CO3 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 Fe3O4@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%.

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Acknowledgements

XPS and TEM studies performed in France (CEA LETI/DTSI/SCMC Grenoble Cedex 9 FRANCE and thanks to N. GAMBACORTI for the organization of XPS and TEM analysis) within the framework of the NFFA-Europe Transnational Access Activity (NFFA Project ID: 723).

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Authors and Affiliations

  1. Hekimhan Vocational College, Department of Property Protection and Security, Malatya Turgut Özal University, Hekimhan, Malatya, Turkey

    Mitat Akkoç

  2. Catalysis Research and Application Center, İnönü University, 44280, Malatya, Turkey

    Mitat Akkoç, Nesrin Buğday, İsmail Özdemir & Sedat Yaşar

  3. Faculty of Science and Arts, Department of Physics, İnönü University, 44280, Malatya, Turkey

    Serdar Altın

  4. Faculty of Science and Arts, Department of Chemistry, İnönü University, 44280, Malatya, Turkey

    İsmail Özdemir & Sedat Yaşar

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  1. Mitat Akkoç
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Akkoç, M., Buğday, N., Altın, S. et al. Highly Active Fe3O4@SBA-15@NHC-Pd Catalyst for Suzuki–Miyaura Cross-Coupling Reaction. Catal Lett 152, 1621–1638 (2022). https://doi.org/10.1007/s10562-021-03755-w

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