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Cyanation of aryl bromides with K4[Fe(CN)6] using polydopamine supported Pd nanoparticle catalysis: formation of magnetite during the reaction

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Abstract

We report the application of polydopamine (PDA) supported Pd nanoparticles in the cyanation of aryl halides with inexpensive and non-toxic K4[Fe(CN)6]. We found that Pd/PDA is an efficient catalyst in the reaction of electron poor aryl halides, however, in other cases the addition of tetrabutyl ammonium bromide was necessary for conversion. The main limitation of the system is suggested to be catalyst deactivation due to Pd aggregation, polymer degradation/functionalization under the high temperature required for catalysis. In several cases we found the formation of magnetite upon reaction, suggesting that K4[Fe(CN)6] is giving away all its six CN groups in cyanation reaction.

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Acknowledgements

Financial support from the National Research, Development and Innovation Office, Hungary [NKFIH Grant FK 123760 (GL)] is gratefully acknowledged. GL acknowledges the János Bolyai Research Scholarship from the Hungarian Academy of Sciences. Péter Németh (Institute of Materials and Environmental Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences) is acknowledged for TEM and SEM imaging of PDA. The Chemical Biology Research Group and the Organocatalysis Research Group (both at the Institute of Organic Chemistry Research Centre for Natural Sciences, Hungarian Academy of Sciences) are acknowledged for support.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok körútja 2., Budapest, 1117, Hungary

    Tamás Gazdag, Attila Kunfi & Gábor London

  2. Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, 6720, Hungary

    Attila Kunfi

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  1. Tamás Gazdag
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  2. Attila Kunfi
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  3. Gábor London
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Correspondence to Gábor London.

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Gazdag, T., Kunfi, A. & London, G. Cyanation of aryl bromides with K4[Fe(CN)6] using polydopamine supported Pd nanoparticle catalysis: formation of magnetite during the reaction. Reac Kinet Mech Cat 125, 567–581 (2018). https://doi.org/10.1007/s11144-018-1478-x

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