Hexagonal Boron Nitride Supported N -Heterocyclic Carbene-Palladium(II): A New, Efficient and Recyclable Heterogeneous C
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Hexagonal Boron Nitride Supported N‑Heterocyclic Carbene‑Palladium(II): A New, Efficient and Recyclable Heterogeneous Catalyst for Suzuki–Miyaura Cross‑Coupling Reaction Arnet Maria Antony1 · Vishal Kandathil1 · Manjunatha Kempasiddaiah1 · B. S. Sasidhar2 · Shivaputra A. Patil3 · Siddappa A. Patil1 Received: 16 June 2020 / Accepted: 20 September 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract In this study, a new stable and powerful hexagonal boron nitride supported N-heterocyclic carbene-palladium(II) complex (h-BN@NHC-Pd) heterogeneous catalyst was designed and synthesized. The structure of the h-BN@NHC-Pd heterogeneous catalyst was characterized by various techniques such as Fourier transform infrared spectra (FT-IR), ultraviolet–visible spectroscopy (UV–Visible), inductively coupled plasma-optical emission spectroscopy (ICP-OES), energy-dispersive X-ray spectroscopy (EDS), field-emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), X-ray powder diffraction (XRD), thermogravimetric analysis (TGA) and Brunauer–Emmett–Teller surface area analysis (BET). Then catalytic activity of h-BN@NHC-Pd heterogeneous catalyst was studied in the Suzuki–Miyaura cross-coupling reactions between aryl halides and arylboronic acids in aqueous medium at room temperature. The effects of varying solvents, bases, temperature, time and catalytic ratios on the performance of the Suzuki–Miyaura cross-coupling reaction were investigated. Moreover, h-BN@NHC-Pd heterogeneous catalyst could be easily recovered through simple filtration or centrifugation method and could be reused five times without significant loss of its catalytic efficiency. Furthermore, stability of the h-BN@ NHC-Pd heterogeneous catalyst after recycling was confirmed through FESEM and FT-IR techniques. The h-BN@NHC-Pd heterogeneous catalyst shows remarkable advantages such as simplicity of operation, excellent yields, short reaction times, heterogeneous nature, easily separable and high stability without leaching.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10562-020-03401-x) contains supplementary material, which is available to authorized users. * Siddappa A. Patil [email protected]; [email protected] 1
Centre for Nano and Material Sciences, Jain University, Jain Global Campus, Kanakapura, Ramanagaram, Bangalore 562112, India
2
Organic Chemistry Section, Chemical Sciences & Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR), Thiruvananthapuram, Kerala 695019, India
3
Pharmaceutical Sciences Department, College of Pharmacy, Rosalind Franklin University of Medicine and Science, 3333 Green Bay Road, North Chicago, IL 60064, USA
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Graphic Abstract A new stable and powerful hexagonal boron nitride supported N-heterocyclic carbene-palladium(II) complex (h-BN@NHCPd) heterogeneous catalyst was designed, synthesized, characterized and c
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