Copper Iodide Nanoparticles Immobolized Porous Polysulfonamide: An Effective Nanocatalyst for Synthesis of Imidazo [1,2-

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Copper Iodide Nanoparticles Immobolized Porous Polysulfonamide: An Effective Nanocatalyst for Synthesis of Imidazo [1,2‑a] Pyridines Fatemeh Hamidi Dastjerdi1 · Ramin Ghorbani‑Vaghei1 · Sedigheh Alavinia1 Received: 11 March 2020 / Accepted: 16 May 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020

Abstract An efficient route was developed for the synthesis of a new polymer, porous cross-linked poly(ethyleneamine)-polysulfonamide (PEA-PSA), as an organic support for the imobilization of CuI nanoparticles (PEA-PSA@CuI). The resulting catalyst works as an efficient recyclable heterogeneous catalyst for the synthesis of imidazo[1,2-a] pyridines from the reaction of 2-aminopyridine, aldehydes and phenylacetylene. The method possesses significant advantages including: easy purification, functional group tolerance, recyclability of the catalyst and synthesis of new derivatives in high to excellent yields and short reaction times. Graphic Abstract

Keywords  Porous polysulfonamide · CuI NPs · Heterogeneous · Imidazo[1,2-a]pyridines

1 Introduction A wide variety of research has been done on cuprous iodide (CuI) due to its distinctive features including: large iconicity and band gap, negative spin–orbit splitting, anomalous diamagnetism behaviour, and unusually large temperature dependency [1, 2]. Potential applications of CuI range from Electronic supplementary material  The online version of this article (https​://doi.org/10.1007/s1056​2-020-03265​-1) contains supplementary material, which is available to authorized users. * Ramin Ghorbani‑Vaghei [email protected] 1



Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, 6517838683 Hamadan, Iran

superionic conductors and solid-state solar cells to catalysts for the synthesis of various organic compounds [3]. Besides, various scaffolds have been recently applied in order to assemble and grow copper nanoparticles (Cu-NPs) i.e. Merrifield resin supported phenanthroline copper(I) complex [4], immobilized copper in organic–inorganic hybrid material [5], MCM-41 [6], and glycerol ingrained copper [7]. Owing to the fact that, the organic structure coverage is not a complete one, the NP sized distribution would be broad, and the NPs’ spatial arrangement is irregular [8]. As a result developing novel methods for the synthesis of hybrid structures which aim at controlling the mentioned parameters would be highly desirable. Organic polymers are promising candidates for the matric, due to their ease of processing and handling as compared

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to metals and inorganic glasses [9]. Ligands having sulfonamide groups are excellent in the stabilization of palladium and bromine species [10, 11]. Polysulfonamides are prepared from the reaction between various amines and disulfonyl chloride [10, 11]. In this work, our goal has been to synthesize a novel porous polysulfonamide as a substrate for the stabilization of CuI NPs (PEA-PSA@CuI) [12]. The porousity and coordination interaction between copper and polysulfonamide