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精氨酸-氰基胍功能化磁性g-CN上的银纳米颗粒:一种用于硝基芳烃氢化和区域选择性点击反应的催化剂。

Ag nanoparticles on arginine-cyanoguanidine functionalized magnetic g-CN: A catalyst for nitroaromatic hydrogenation and regioselective click reactions.

作者信息

Daraie Mansoureh, Tajbakhsh Mahmood, Ayati Ali, Rashidi Sara

机构信息

Department of Chemistry, Science and Research Branch, Islamic Azad University, P.O. Box 14515/775, Tehran, Iran.

Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, Iran.

出版信息

Heliyon. 2024 Oct 5;10(19):e38956. doi: 10.1016/j.heliyon.2024.e38956. eCollection 2024 Oct 15.

Abstract

This study describes the development of a novel hybrid nanocatalyst that was obtained by doping magnetic g-CN with Ag nanoparticles and modifying it with arginine and cyanoguanidine (Ag@FeO-g-CN-Arg-CG). Comprehensive characterization of the nanocatalyst using techniques such as FTIR, XRD, SEM, and TGA confirmed its structural and morphological properties. The catalytic efficiency of the synthesized nanostructure was evaluated in two key reactions: the reduction of nitroaromatic compounds and a click reaction for 1,2,3-triazole synthesis. The results demonstrate that Ag@FeO-g-CN-Arg-CG effectively reduced various nitroaromatic compounds to substituted anilines at room temperature using NaBH as the reducing agent. Nitrobenzene reduction did not proceed in aprotic solvents such as acetonitrile, CHCl, and dimethylformamide, whereas it exhibited a high reaction yield in protic solvents such as ethanol and water. The highest yield (100 %) was observed in water at 50 °C using HO solvent. Additionally, the nanohybrid exhibited significant potential for "green" click chemistry by efficiently synthesizing 1,2,3-triazoles under mild conditions, with low catalyst loading. Its magnetic properties facilitated easy recovery, and the catalyst maintained high activity over six cycles, making it suitable for sustainable applications in organic transformations.

摘要

本研究描述了一种新型杂化纳米催化剂的开发,该催化剂是通过用银纳米颗粒掺杂磁性石墨相氮化碳并使用精氨酸和氰基胍对其进行改性而获得的(Ag@FeO-g-CN-Arg-CG)。使用傅里叶变换红外光谱(FTIR)、X射线衍射(XRD)、扫描电子显微镜(SEM)和热重分析(TGA)等技术对该纳米催化剂进行的全面表征证实了其结构和形态特性。在两个关键反应中评估了合成纳米结构的催化效率:硝基芳烃化合物的还原反应以及用于1,2,3-三唑合成的点击反应。结果表明,以硼氢化钠(NaBH)作为还原剂,Ag@FeO-g-CN-Arg-CG在室温下能有效地将各种硝基芳烃化合物还原为取代苯胺。在非质子溶剂如乙腈、三氯甲烷和二甲基甲酰胺中,硝基苯的还原反应无法进行,而在质子溶剂如乙醇和水中,该反应具有较高的产率。在50℃使用水作为溶剂时,在水中观察到了最高产率(100%)。此外,该纳米杂化物通过在温和条件下以低催化剂负载量高效合成1,2,3-三唑,在“绿色”点击化学方面展现出显著潜力。其磁性便于回收,并且该催化剂在六个循环中均保持高活性,使其适用于有机转化的可持续应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d681/11491912/8d591c391d22/sc1.jpg

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