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一种在无碱和无配体条件下叠氮阴离子与芳基卤化物交叉偶联的绿色路线:CuO-CuO-Cu-C纳米复合材料的卓越性能

A green route for the cross-coupling of azide anions with aryl halides under both base and ligand-free conditions: exceptional performance of a CuO-CuO-Cu-C nanocomposite.

作者信息

Karimzadeh Morteza, Niknam Khodabakhsh, Manouchehri Neda, Tarokh Dariush

机构信息

Department of Chemistry, Faculty of Sciences, Persian Gulf University Bushehr 75169 Iran

出版信息

RSC Adv. 2018 Jul 18;8(45):25785-25793. doi: 10.1039/c8ra04608e. eCollection 2018 Jul 16.

Abstract

A convenient, inexpensive and effective route for the preparation of a CuO-CuO-Cu-C nanocomposite is described here by applying Cu(ii) as a source of copper. Characterization of the nanocomposite was performed with X-ray diffraction (XRD), Fourier-transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), high-resolution TEM (HR-TEM), field emission scanning electron microscopy (FE-SEM), X-ray photoelectron spectroscopy (XPS), and energy-dispersive X-ray spectroscopy (EDX). Analysis of the data showed that the particles of the nanocomposite are uniformly distributed and show high catalytic activity in the cross-coupling of sodium azide with various aryl iodides and bromides. This nanocomposite has a high level of performance, and even led to the synthesis of the products at room temperature. In addition, this is the first report of the synthesis of aryl azides under both base- and ligand-free conditions. For the first time, both ligand- and base-free conditions were applied for the synthesis of aryl azides, which implies exceptional performance of the CuO-CuO-Cu-C nanocomposite. Simultaneous removal of the base and ligand in a green solvent is the main advantage of this reaction. Unfortunately, aryl bromides and aryl iodides with electron-withdrawing functional groups in their scaffold did not give the desired aryl azides.

摘要

本文描述了一种便捷、廉价且有效的制备CuO-CuO-Cu-C纳米复合材料的方法,该方法以Cu(ii)作为铜源。通过X射线衍射(XRD)、傅里叶变换红外光谱(FT-IR)、透射电子显微镜(TEM)、高分辨率TEM (HR-TEM)、场发射扫描电子显微镜(FE-SEM)、X射线光电子能谱(XPS)和能量色散X射线光谱(EDX)对该纳米复合材料进行了表征。数据分析表明,该纳米复合材料的颗粒分布均匀,在叠氮化钠与各种芳基碘化物和溴化物的交叉偶联反应中表现出高催化活性。这种纳米复合材料具有很高的性能,甚至能在室温下合成产物。此外,这是在无碱和无配体条件下合成芳基叠氮化物的首次报道。首次将无配体和无碱条件应用于芳基叠氮化物的合成,这意味着CuO-CuO-Cu-C纳米复合材料具有卓越的性能。在绿色溶剂中同时去除碱和配体是该反应的主要优点。不幸的是,在其骨架中带有吸电子官能团的芳基溴化物和芳基碘化物未能得到所需的芳基叠氮化物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eda2/9082577/20ff56496101/c8ra04608e-f1.jpg

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