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一种新型铜(II)纳米磁性N-双席夫碱配合物的合成及其作为点击合成四氮唑的高效催化剂

Synthesis of a novel nanomagnetic N bis schiff base complex of copper(ii) as an efficient catalyst for click synthesis of tetrazoles.

作者信息

Hsu Chou-Yi, AlBajalan Ahmed Rafiq, Awad Sameer A, Suliman Muath, Juraev Nizomiddin, Rodriguez-Benites Carlos, AlMohamadi Hamad, Kadhim Abed J

机构信息

Thunderbird School of Global Management, Arizona State University Tempe Campus Phoenix Arizona 85004 USA.

Petroleum Technology Department, Erbil Polytechnic University Erbil Kurdistan Region Iraq

出版信息

Nanoscale Adv. 2024 Oct 25;6(24):6408-19. doi: 10.1039/d4na00642a.

DOI:10.1039/d4na00642a
PMID:39502108
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11533056/
Abstract

In this study, we have prepared a novel bis-Schiff-base copper(ii) complex by modifying FeO with acetylacetone functionalities and subsequently forming a Schiff base with 2-picolylamine and CuCl through a template method. Immobilization of 2,4-pentanedione and its reaction with 2-picolylamine enabled the synthesis of 1,3-diketimines (HNacNac) as an anionic ligand. This unique design resulted in a tetradentate N coordination sphere for copper(ii) ion complexation. The resulting heterogeneous catalyst, [FeO@Sil-Schiff-base-Cu(ii)], efficiently catalyzed the click condensation of diverse aryl nitriles with sodium azide to produce 5-substituted 1-tetrazoles in high yields and selectivity. The catalyst demonstrated remarkable stability and recyclability without appreciable loss of catalytic activity, as confirmed by hot filtration and reusability studies.

摘要

在本研究中,我们通过用乙酰丙酮官能团修饰FeO,随后通过模板法与2-吡啶甲胺和CuCl形成席夫碱,制备了一种新型双席夫碱铜(II)配合物。固定2,4-戊二酮并使其与2-吡啶甲胺反应,使得能够合成作为阴离子配体的1,3-二酮亚胺(HNacNac)。这种独特的设计产生了用于铜(II)离子络合的四齿N配位球。所得的多相催化剂[FeO@Sil-席夫碱-Cu(II)]有效地催化了各种芳基腈与叠氮化钠的点击缩合反应,以高产率和选择性生成5-取代的1-四唑。热过滤和可重复使用性研究证实,该催化剂表现出显著的稳定性和可回收性,且催化活性没有明显损失。

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