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Palladium Loaded Dendronized Polymer as Efficient Polymeric Sustainable Catalyst for Heck Coupling Reaction

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Abstract

The palladium incorporated amine-functionalized dendronized polymer was synthesized by the addition of palladium acetate to dendronized polymer in methanol at room temperature. Palladium species are immobilized onto the dendritic structure by their coordination with amino functional groups. The newly developed dendritic system showed high palladium content in the low generation level itself, which was found to be 4.19 mmol/g. This was fairly higher than, the other palladium-based catalysts. Energy dispersive X-ray spectroscopy, Fourier transform infrared spectroscopy, UV–Visible spectroscopy, and X-ray photoelectron spectroscopy were used to confirm the successful synthesis of the new catalyst. It was used as a homogeneous palladium catalyst for Heck coupling reaction between olefins and differently substituted aryl halides and the products were isolated in high yield. The products isolated were in trans configuration, which indicated the selectivity of the newly developed catalytic system. Also, this catalyst system was reused up to nine times without a significant decrease in its catalytic activity. The easy accessibility of catalytic sites, stability, resistance to metal leaching, high catalytic activity and remarkable stereoselectivity with a low amount of catalyst are all due to the dendritic support. The docking study was carried out for all the stilbene derivatives obtained by the Heck coupling reaction against DprE1 protein to study its potential antitubercular activity. All the compounds displayed superior docking score values over the range − 6.5 to − 8.2 kcal/mol, compared to the standard drug isoniazid with docking score of − 6.1 kcal/mol against DprE1.

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Acknowledgements

Hiba K. gratefully acknowledges UGC, New Delhi, India for financial support in the form of a Senior Research Fellowship and for the support under SAP DRS-III. The authors are thankful to the Sophisticated Analytical Instrumentation Facility (SAIF), CUSAT, Kochi for EDX, and Department of Physics for FE-SEM analysis. We thank CLIF, University of Kerala for XPS, and IIRBS, Mahatma Gandhi University for NMR analysis.

Funding

This work was supported by the University Grants Commission (Grant No. Ref. No: 21/12/2014 (ii) EU-V).

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  1. Department of Applied Chemistry, Cochin University of Science and Technology, Kochi, 682022, India

    K. Hiba, G. Anjali Krishna, S. Prathapan & K. Sreekumar

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  1. K. Hiba
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  2. G. Anjali Krishna
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GC–MS, 1H NMR, 13C NMR of compounds

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Hiba, K., Krishna, G.A., Prathapan, S. et al. Palladium Loaded Dendronized Polymer as Efficient Polymeric Sustainable Catalyst for Heck Coupling Reaction. Catal Lett 152, 1819–1834 (2022). https://doi.org/10.1007/s10562-021-03767-6

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