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A green route for the cross-coupling of azide anions with aryl halides under both base and ligand-free conditions: exceptional performance of a Cu(2)O–CuO–Cu–C nanocomposite

A convenient, inexpensive and effective route for the preparation of a Cu(2)O–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), transmis...

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Autores principales: Karimzadeh, Morteza, Niknam, Khodabakhsh, Manouchehri, Neda, Tarokh, Dariush
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9082577/
https://www.ncbi.nlm.nih.gov/pubmed/35539779
http://dx.doi.org/10.1039/c8ra04608e
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author Karimzadeh, Morteza
Niknam, Khodabakhsh
Manouchehri, Neda
Tarokh, Dariush
author_facet Karimzadeh, Morteza
Niknam, Khodabakhsh
Manouchehri, Neda
Tarokh, Dariush
author_sort Karimzadeh, Morteza
collection PubMed
description A convenient, inexpensive and effective route for the preparation of a Cu(2)O–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 Cu(2)O–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.
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spelling pubmed-90825772022-05-09 A green route for the cross-coupling of azide anions with aryl halides under both base and ligand-free conditions: exceptional performance of a Cu(2)O–CuO–Cu–C nanocomposite Karimzadeh, Morteza Niknam, Khodabakhsh Manouchehri, Neda Tarokh, Dariush RSC Adv Chemistry A convenient, inexpensive and effective route for the preparation of a Cu(2)O–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 Cu(2)O–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. The Royal Society of Chemistry 2018-07-18 /pmc/articles/PMC9082577/ /pubmed/35539779 http://dx.doi.org/10.1039/c8ra04608e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Karimzadeh, Morteza
Niknam, Khodabakhsh
Manouchehri, Neda
Tarokh, Dariush
A green route for the cross-coupling of azide anions with aryl halides under both base and ligand-free conditions: exceptional performance of a Cu(2)O–CuO–Cu–C nanocomposite
title A green route for the cross-coupling of azide anions with aryl halides under both base and ligand-free conditions: exceptional performance of a Cu(2)O–CuO–Cu–C nanocomposite
title_full A green route for the cross-coupling of azide anions with aryl halides under both base and ligand-free conditions: exceptional performance of a Cu(2)O–CuO–Cu–C nanocomposite
title_fullStr A green route for the cross-coupling of azide anions with aryl halides under both base and ligand-free conditions: exceptional performance of a Cu(2)O–CuO–Cu–C nanocomposite
title_full_unstemmed A green route for the cross-coupling of azide anions with aryl halides under both base and ligand-free conditions: exceptional performance of a Cu(2)O–CuO–Cu–C nanocomposite
title_short A green route for the cross-coupling of azide anions with aryl halides under both base and ligand-free conditions: exceptional performance of a Cu(2)O–CuO–Cu–C nanocomposite
title_sort green route for the cross-coupling of azide anions with aryl halides under both base and ligand-free conditions: exceptional performance of a cu(2)o–cuo–cu–c nanocomposite
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9082577/
https://www.ncbi.nlm.nih.gov/pubmed/35539779
http://dx.doi.org/10.1039/c8ra04608e
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