Efficient one-pot synthesis of 1,4-disubstituted-1,2,3-triazoles catalysed by NiO/Cu2O/CuO nanocomposites under microwave irradiation

IF 2.2 4区 化学 Q2 Engineering Chemical Papers Pub Date : 2024-08-19 DOI:10.1007/s11696-024-03640-x
Yasser M. A. Mohamed, Shams H. Abdel-Hafez, Hassan Elsayed, Mohamed Taha, Yasser A. Attia
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Abstract

The Cu-catalysed azide-alkyne cycloaddition (CuAAC) reaction, also known as the “click” reaction, is a powerful tool in organic synthesis due to its high efficiency, regioselectivity, and mild reaction conditions. However, the use of homogeneous copper catalysts often leads to challenges like separation and disposal, limiting their applicability in industrial settings. This study aimed to develop a novel heterogeneous catalyst utilizing NiO/Cu2O/CuO nanocomposites (NCs) for the selective and efficient synthesis of 1,4-disubstituted-1,2,3-triazoles via the click reaction. NiO/Cu2O/CuO NCs were prepared by a simple co-precipitation method. The catalytic activity of the prepared NCs was evaluated for the one-pot, three-component click reaction between benzyl bromide analogues, sodium azide, and phenyl acetylene under various conditions: ambient temperature, thermal heating, and microwave irradiation. The reaction progress was monitored by TLC, and the products were isolated and characterized by SEM, FTIR, XRD, and XPS. The NiO/Cu2O/CuO NCs exhibited superior catalytic performance compared to Cu2O/CuO nanoparticles (NPs). They facilitated the exclusive formation of the desired 1,4-isomer under all tested conditions. Notably, under microwave irradiation, the NiO/Cu2O/CuO NCs delivered significantly higher yields (89–96%) compared to Cu2O/CuO NPs (76–82%) for diverse triazole compounds. Characterization confirmed the successful synthesis of the NCs and the purity of the triazole products. Utilizing water as the solvent under microwave irradiation offered several advantages, including faster reaction rates, higher yields, efficient product isolation, and excellent recyclability of the catalyst. This study demonstrates the effectiveness of NiO/Cu2O/CuO NCs as a novel heterogeneous catalyst for the selective and efficient synthesis of 1,4-disubstituted-1,2,3-triazoles. The simple and efficient method, coupled with the advantages of water as a solvent and microwave-assisted heating, presents significant potential for various applications in organic synthesis and beyond.

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微波辐照下 NiO/Cu2O/CuO 纳米复合材料催化的 1,4-二取代-1,2,3-三唑的高效一锅合成
铜催化的叠氮-炔环加成反应(CuAAC),又称 "点击 "反应,因其高效率、区域选择性和温和的反应条件而成为有机合成的有力工具。然而,均相铜催化剂的使用往往会带来分离和处理等难题,限制了其在工业环境中的应用。本研究旨在开发一种新型异相催化剂,利用 NiO/Cu2O/CuO 纳米复合材料(NCs)通过点击反应选择性地高效合成 1,4-二取代的-1,2,3-三唑。NiO/Cu2O/CuO 纳米复合材料是通过简单的共沉淀法制备的。在常温、热加热和微波辐照等不同条件下,评估了所制备的 NCs 对苄基溴类似物、叠氮化钠和苯乙炔之间的一锅三组分点击反应的催化活性。反应过程通过 TLC 进行监控,产物被分离出来并通过 SEM、FTIR、XRD 和 XPS 进行表征。与 Cu2O/CuO 纳米颗粒(NPs)相比,NiO/Cu2O/CuO NCs 表现出更优越的催化性能。在所有测试条件下,它们都能促进所需的 1,4 异构体的生成。值得注意的是,与 Cu2O/CuO NPs(76-82%)相比,在微波辐照下,NiO/Cu2O/CuO NCs 的产率(89-96%)明显高于 Cu2O/CuO NPs(76-82%)。表征证实了 NCs 的成功合成和三唑产品的纯度。在微波辐照下利用水作为溶剂具有多种优势,包括反应速度更快、产率更高、产品分离效率高以及催化剂具有良好的可回收性。本研究证明了 NiO/Cu2O/CuO NCs 作为新型异相催化剂选择性高效合成 1,4-二取代-1,2,3-三唑的有效性。该方法简单高效,加上以水为溶剂和微波辅助加热的优势,在有机合成及其他领域的各种应用中具有巨大潜力。
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来源期刊
Chemical Papers
Chemical Papers Chemical Engineering-General Chemical Engineering
CiteScore
3.30
自引率
4.50%
发文量
590
期刊介绍: Chemical Papers is a peer-reviewed, international journal devoted to basic and applied chemical research. It has a broad scope covering the chemical sciences, but favors interdisciplinary research and studies that bring chemistry together with other disciplines.
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