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用于绿色叠氮化物-炔烃环加成反应和乌尔曼反应的超声辅助铜(II)斯特雷克功能化有机催化剂

Ultrasound-assisted Cu(II) Strecker-functionalized organocatalyst for green azide-alkyne cycloaddition and Ullmann reactions.

作者信息

Aghajani Mahyar, Dabiri Minoo

机构信息

Department of Organic Chemistry and Oil, Faculty of Chemistry and Petroleum Sciences, Shahid Beheshti University, Tehran, 1983969411, Islamic Republic of Iran.

出版信息

Sci Rep. 2024 May 27;14(1):12141. doi: 10.1038/s41598-024-62826-1.

DOI:10.1038/s41598-024-62826-1
PMID:38802456
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11130308/
Abstract

A new aminonitrile-functionalized FeO has been synthesized via the Strecker reaction, the designed aminonitrile ligand on the surface of the magnetic core coordinated to copper(II) to obtain the final new catalyst. The fabricated nanocatalyst was characterized by Fourier transform Infrared (FT-IR), Field Emission Scanning Electron Microscopy (FESEM), Energy-Dispersive X-ray spectroscopy (EDX), Transmission Electron Microscopy (TEM), Vibrating-Sample Magnetometer (VSM), Inductively Coupled Plasma Optical Emission Spectroscopy (ICP-OES), and Thermogravimetric Analysis (TGA). The high tendency of nitrogens in the aminonitrile functional group to make a complex with Cu(II) has caused the practical activity of this nucleus in this catalyst. This nanocatalyst performance was investigated in azide-alkyne Huisgen cycloaddition (3 + 2) reaction for achieving to 1,4-disubstituted 1,2,3-triazoles in water as a green media at room temperature. In another try, Classic Ullmann Reaction was investigated for the synthesis of biaryls at 85 °C promoted by ultrasonic condition (37 kHz). The reaction scope was explored using different reactants and the results of using this developed catalytic system demonstrated its capacity to reduce the reaction time and enhance the reaction efficiency to provide good to excellent product yield. Conversely, the simple recycling and reusability of this catalyst for at least six times without any noticeable leaching of copper makes it a potential future catalyst for synthesizing such compounds.

摘要

通过施特雷克反应合成了一种新型的氨基腈功能化的FeO,在磁核表面设计的氨基腈配体与铜(II)配位,从而获得最终的新型催化剂。通过傅里叶变换红外光谱(FT-IR)、场发射扫描电子显微镜(FESEM)、能量色散X射线光谱(EDX)、透射电子显微镜(TEM)、振动样品磁强计(VSM)、电感耦合等离子体发射光谱(ICP-OES)和热重分析(TGA)对制备的纳米催化剂进行了表征。氨基腈官能团中的氮与Cu(II)形成配合物的倾向很高,这导致了该核在这种催化剂中的实际活性。研究了该纳米催化剂在叠氮化物-炔烃惠斯根环加成(3 + 2)反应中的性能,以在室温下作为绿色介质的水中实现1,4-二取代的1,2,3-三唑。在另一次尝试中,研究了经典的乌尔曼反应,在超声条件(37 kHz)下于85°C合成联芳基化合物。使用不同的反应物探索了反应范围,使用这种开发的催化体系的结果表明其有能力缩短反应时间并提高反应效率,以提供良好至优异的产物产率。相反,这种催化剂至少可以简单回收和重复使用六次,而没有任何明显的铜浸出,这使其成为未来合成此类化合物的潜在催化剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3b5/11130308/bae0206c752d/41598_2024_62826_Fig11_HTML.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3b5/11130308/dc31baabcb65/41598_2024_62826_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3b5/11130308/2a476c016fb7/41598_2024_62826_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3b5/11130308/880bf64fe7b1/41598_2024_62826_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3b5/11130308/b34ead4245b5/41598_2024_62826_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3b5/11130308/791c0dd8aedd/41598_2024_62826_Fig9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3b5/11130308/64df2260a868/41598_2024_62826_Fig10_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f3b5/11130308/bae0206c752d/41598_2024_62826_Fig11_HTML.jpg

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6
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