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Reduction of olefins, nitroarenes and Schiff base compounds by a polymer-supported [2-(2′-pyridyl)benzimidazole]palladium complex

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Abstract

2-(2′-Pyridyl)benzimidazole (PBIMH) was functionalized onto chloromethylated polystyrene beads crosslinked with 6.5 % divinylbenzene, and this solid support was then reacted with Na2PdCl4 in methanol. The functionalized beads were then activated using sodium borohydride. The resultant polymer-supported [2-(2′-pyridyl)benzimidazole]palladium complex (PSDVB–PBIM–PdCl2) and its activated form were characterized by various physicochemical techniques. XPS studies confirmed the +2 oxidation state of palladium in the supported complex. The activated complex was found to catalyse the hydrogenation of various organic substrates including olefins, nitro and Schiff base compounds. Kinetic measurements for the hydrogenation of cyclopentene, cyclohexene and cyclooctene were carried out by varying temperature, catalyst and substrate concentration. The energy and entropy of activation were evaluated from the kinetic data. The catalyst showed an excellent recycling efficiency over six cycles without leaching of metal from the polymer support, whereas the unsupported complex was unstable as metal leached out into the solution during the first run.

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Acknowledgments

Authors wish to thank UGC, New Delhi, India, for Major Research Project [F No. 39-741/2010(SR)]. Department of Chemistry, Bangalore University, Bangalore, for instrumentation facilities and Thermax Ltd. for providing PSDVB are gratefully acknowledged. Authors gratefully thank Dr. M. S. Hedge for XPS studies. Authors also thank Prof. Puttaswamy, Dept. of Chemistry, Bangalore University, Bangalore, for his kind help in deriving reaction mechanism and rate law equation.

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  1. Department of Studies in Chemistry, Central College Campus, Bangalore University, Ambedkar Veedi, Bangalore, Karnataka, 560 001, India

    M. L. Shilpa & V. Gayathri

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  1. M. L. Shilpa
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  2. V. Gayathri
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Correspondence to V. Gayathri.

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Shilpa, M.L., Gayathri, V. Reduction of olefins, nitroarenes and Schiff base compounds by a polymer-supported [2-(2′-pyridyl)benzimidazole]palladium complex. Transition Met Chem 41, 393–401 (2016). https://doi.org/10.1007/s11243-016-0035-6

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