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Functionalization of the magnetic chitosan support with dipyridylamine as a nitrogen-rich pincer ligand for Pd immobilization and investigation of catalytic efficiency in Sonogashira coupling

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Abstract

In this study, at first a NNN pincer type ligand was synthesized through the nucleophilic substitution reaction of 2,2′-dipyridylamine with trichloro-1,3,5-triazine in 2:1 ratio. In the next step, the magnetic chitosan biosupport was reacted with this nitrogen-rich ligand that provided coordinative sites for the palladium complexation. The prepared nanocomposite (Fe3O4@DPA-CS@NNN-Pd0) was identified by different analysis including FT-IR, XRD, EDX, FESEM, DLS, VSM and ICP. Then, its catalytic activity was examined in the Sonogashira coupling reaction. The related products were produced in a short reaction time with proper yields. Moreover, the nanocatalyst can be magnetically separated and reused for four successive runs with no noticeable loss in its catalytic activity.

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  1. Department of Organic Chemistry, Faculty of Chemistry, Alzahra University, Tehran, Iran

    F. Rafiee & M. Rezaee

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Rafiee, F., Rezaee, M. Functionalization of the magnetic chitosan support with dipyridylamine as a nitrogen-rich pincer ligand for Pd immobilization and investigation of catalytic efficiency in Sonogashira coupling. Polym. Bull. 80, 11139–11154 (2023). https://doi.org/10.1007/s00289-022-04597-1

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