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Suzuki–Miyaura reaction and solventfree oxidation of benzyl alcohol by Pd/nitrogen-doped CNTs catalyst

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Abstract

Suzuki–Miyaura C–C coupling reactions were investigated with Pd/nitrogen-doped carbon nanotubes (Pd/N-CNTs) as a catalyst. Also, the same catalyst was examined for the solventfree oxidation of benzyl alcohol to benzaldehyde. Nitrogen-doped carbon nanotubes (N-CNTs) were synthesized from 1-ferrocenylmethyl(2-methylimidazole) and benzophenone via a chemical vapour deposition technique. Acetonitrile was used as a solvent and source of both carbon and nitrogen constituents of N-CNTs. Pd nanoparticles (Pd NPs) were successfully dispersed on N-CNTs via a metal organic chemical vapour deposition method. SEM, TEM, XRD, elemental analysis and ICP-OES measurements were used to characterize the nanomaterials. From the TEM analysis, it was observed that Pd NPs were spherical and with particle sizes ranging from 3 to 8 nm. For Suzuki C–C coupling reactions, phenylboronic acid, aryl halide, Pd/N-CNTs catalyst and a base (NaOAc, K2PO4, K2CO3, NaOH, Et3N and Na2CO3) were used. The optimized experiments indicate that K2CO3, as the base, and ethanol/water (1:1 v/v, 10 mL) mixture, as a solvent, are the best reaction conditions. The solventfree oxidation reactions of benzyl alcohol were also done with Pd/N-CNTs catalyst and benzyl alcohol as a substrate. In both sets of reactions, C–C coupling and oxidation, the increase in pyrrolic nitrogen species was found to be responsible for higher catalytic activities of Pd/N-CNT catalysts, and this was attributed to the ease of Pd NP dispersion on N-CNTs, relative to pristine CNTs. Also, the higher catalytic activity of Pd/N-CNTs could be ascribed not only to the smaller Pd NP size or surface area, but to also the surface properties and the nature of the support when compared with the undoped counterpart, Pd/CNTs.

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Acknowledgements

This research was financially supported by the National Research Foundation (NRF) South Africa, Grant Number 103979. We are grateful to the School of Chemistry and Physics, University of KwaZulu-Natal (UKZN), for creating a conducive research laboratory for this work. Ayomide is grateful to Mrs Rashidat Labulo and Dr Moses Ollengo for proofreading this manuscript.

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  1. School of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban, South Africa

    Ayomide H. Labulo, Bernard Omondi & Vincent O. Nyamori

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  1. Ayomide H. Labulo
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  2. Bernard Omondi
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  3. Vincent O. Nyamori
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Correspondence to Vincent O. Nyamori.

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Labulo, A.H., Omondi, B. & Nyamori, V.O. Suzuki–Miyaura reaction and solventfree oxidation of benzyl alcohol by Pd/nitrogen-doped CNTs catalyst. J Mater Sci 53, 15817–15836 (2018). https://doi.org/10.1007/s10853-018-2748-8

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