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Efficient Synthesis of Novel Phenanthroline-Dimedone Derivatives Using Pd@Hqbi-Spion As a Versatile Palladium-Immobilized Catalyst Publisher Pubmed



Sayahi MH1 ; Serajian A2 ; Bahadorikhalili S3 ; Mahdavi M4
Authors
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Authors Affiliations
  1. 1. Department of Chemistry, Payame Noor University, Tehran, Iran
  2. 2. Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Zanjan, Iran
  3. 3. Department of Electronic Engineering, Universitat Rovira i Virgili, Tarragona, 43007, Spain
  4. 4. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: Scientific Reports Published:2024


Abstract

This paper presents the synthesis and application of a novel catalyst for carbon–carbon bond formations, comprising palladium immobilized on 2-(5-hydroxyquinolin-8-yl)-1H-benzo[d]imidazole-5-carboxylic acid modified superparamagnetic iron oxide nanoparticles (Pd@HQBI-SPION). The synthesis involved the attachment of HQBI ligands to SPION using APTES, followed by the immobilization of palladium. Characterization techniques, including FTIR, TEM, and magnetic measurements, confirmed the successful synthesis and structural integrity of Pd@HQBI-SPION. The catalytic activity of Pd@HQBI-SPION was evaluated in various carbon–carbon bond formation reactions, demonstrating high efficiency and reusability. 8 different derivatives bearing several electron withdrawing and electron donating functionalities were used as starting materials and the products were obtained in high isolated yields (75–97%). The catalyst exhibited excellent performance in one-pot synthesis of phenanthroline-dimedone polycyclic derivatives via C-alkylation followed by intramolecular O-alkylation of phenanthroline with dimedone. The products are obtained in high to excellent yields is described. This protocol presents a highly selective synthetic method for the construction of polycyclic aromatic compounds containing nitrogen and oxygen atoms. © The Author(s) 2024.
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