Yasser M. A. Mohamed, Shams H. Abdel-Hafez, Hassan Elsayed, Mohamed Taha, Yasser A. Attia
{"title":"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","authors":"Yasser M. A. Mohamed, Shams H. Abdel-Hafez, Hassan Elsayed, Mohamed Taha, Yasser A. Attia","doi":"10.1007/s11696-024-03640-x","DOIUrl":null,"url":null,"abstract":"<div><p>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/Cu<sub>2</sub>O/CuO nanocomposites (NCs) for the selective and efficient synthesis of 1,4-disubstituted-1,2,3-triazoles via the click reaction. NiO/Cu<sub>2</sub>O/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/Cu<sub>2</sub>O/CuO NCs exhibited superior catalytic performance compared to Cu<sub>2</sub>O/CuO nanoparticles (NPs). They facilitated the exclusive formation of the desired 1,4-isomer under all tested conditions. Notably, under microwave irradiation, the NiO/Cu<sub>2</sub>O/CuO NCs delivered significantly higher yields (89–96%) compared to Cu<sub>2</sub>O/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/Cu<sub>2</sub>O/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.</p></div>","PeriodicalId":513,"journal":{"name":"Chemical Papers","volume":null,"pages":null},"PeriodicalIF":2.2000,"publicationDate":"2024-08-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Efficient one-pot synthesis of 1,4-disubstituted-1,2,3-triazoles catalysed by NiO/Cu2O/CuO nanocomposites under microwave irradiation\",\"authors\":\"Yasser M. A. Mohamed, Shams H. Abdel-Hafez, Hassan Elsayed, Mohamed Taha, Yasser A. Attia\",\"doi\":\"10.1007/s11696-024-03640-x\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>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/Cu<sub>2</sub>O/CuO nanocomposites (NCs) for the selective and efficient synthesis of 1,4-disubstituted-1,2,3-triazoles via the click reaction. NiO/Cu<sub>2</sub>O/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/Cu<sub>2</sub>O/CuO NCs exhibited superior catalytic performance compared to Cu<sub>2</sub>O/CuO nanoparticles (NPs). They facilitated the exclusive formation of the desired 1,4-isomer under all tested conditions. Notably, under microwave irradiation, the NiO/Cu<sub>2</sub>O/CuO NCs delivered significantly higher yields (89–96%) compared to Cu<sub>2</sub>O/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/Cu<sub>2</sub>O/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.</p></div>\",\"PeriodicalId\":513,\"journal\":{\"name\":\"Chemical Papers\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.2000,\"publicationDate\":\"2024-08-19\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemical Papers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s11696-024-03640-x\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"Engineering\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Papers","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11696-024-03640-x","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Engineering","Score":null,"Total":0}
Efficient one-pot synthesis of 1,4-disubstituted-1,2,3-triazoles catalysed by NiO/Cu2O/CuO nanocomposites under microwave irradiation
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.
Chemical PapersChemical 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.