Reusable Cu2O-Nanoparticle-Catalyzed Amidation of Aryl Iodides (original) (raw)
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Copper-Catalyzed Amidation of Aryl Iodides in the Presence of Various Chelating Ligands
Journal of the Chinese Chemical Society, 2008
N,N¢-Dibenzylethylenediamine is presented as a new, efficient, and versatile bidentate ligand suitable for the copper catalyzed formation of the C-N bond. This bidentate ligand has been demonstrated to facilitate the copper catalyzed cross-coupling reactions of aryl iodides with amides to afford the desired products in good to excellent yields.
A B S T R A C T An efficient and multicomponent method has been developed for the synthesis of functionalized tricarboxamides at room temperature using CuI nanoparticles as catalyst. This method involved fivecomponent coupling reactions of Meldrum's acid, isocyanides with aromatic aldehydes and amines at room temperature. Atom economy, wide range of products, excellent yields in short time and mild reaction conditions are some of the important features of this protocol. Notably, this catalyst could be recycled and reused for several times without significantly decreasing the catalytic activity.
Synthesis and Characterization of Cu Nanoparticles and Studying of Their Catalytic Properties
international journal of nano dimension, 2012
In this paper, we report on the synthesis of Cu nanoparticles through a single-precursor route by controlling the growth temperature. Selective adsorption of oleylamine on various crystal planes may play an important role in the growth process. The understanding of this selfassembling process will help us develop reliable and reproducible methods to synthesis other three dimensional nanostructured architectures and increase the knowledge of self-assembly. The catalytic activities of these nanoparticles of different sizes have been tested on the yield of production of biphenyl from the iodobenzene in reaction. The as synthesized products were characterized by powder X-Ray diffraction (XRD), Scanning electron microscopy (SEM), Energy-dispersive X-ray (EDX) analysis and UV-vis spectra.
ChemCatChem, 2019
A series of catalysts based on supported copper nanoparticles have been prepared and tested in the amide bond formation from tertiary amines and acid anhydrides, in the presence of tert-butyl hydroperoxide as an oxidant. Copper nanoparticles on zeolite Y (CuNPs/ZY) was found to be the most efficient catalyst for the synthesis of amides, working in acetonitrile as solvent, under ligand-and base-free conditions in air. The products were obtained in good to excellent yields and in short reaction times. The CuNPs/ZY system also exhibited higher catalytic activity than some commercially available copper and iron sources and it was reused in ten reaction cycles without any further pre-treatment. This methodology has been successfully scaled-up to a gram scale with no detriment to the yield. Supporting information for this article is given via a link at the end of the document.
The application of magnetic CuFe2O4 nanoparticles for the oxidative amidation of aldehydes with amine hydrochloride salts is described. A wide range of amides have been synthesized in good to excellent yields under mild conditions. Chiral amide also synthesized from its corresponding chiral amine salt with retention of the stereochemistry. In particular, the performance of the magnetic separation of the catalyst was very efficient and an alternative to time, solvent and energy-consuming separation procedures. The catalytic activity of the catalyst remains unaltered after five consecutive cycles, making it environmentally benign and widely applicable due to its efficiency, ease of handling and cost effectiveness
An efficient, reusable copper-oxide/carbon-nanotube catalyst for N-arylation of imidazole
Carbon, 2013
Copper oxide nanoparticles (CuONPs) were successfully decorated on acid treated multiwall carbon nanotubes (f-MWCNTs) using copper acetate precursor by a very simple ''mix and heat'' method, and was used as a heterogeneous nanocatalyst for the N-arylation of imidazole for the first time. The transmission electron microscopic (TEM) images of the prepared nanocatalyst (CuO/MWCNT) showed a good adhesion of CuONPs on anchoring sites of the MWCNTs. The factual loading of Cu in CuO/MWCNT was 7.64 wt% as confirmed by inductively coupled plasma-mass spectrometry (ICP-MS). The chemical state of Cu on MWCNTs was +2 as revealed by wide angle X-ray diffraction (WAXD), X-ray photoelectron spectroscopic (XPS) and temperature programmed reduction (TPR) techniques. Initially the reaction conditions were optimized and then the scope of the catalytic system was extended with different aryl halides. 0.98 mol% (5 mg) of the catalyst was sufficient for N-arylation of imidazole. A literature survey showed that this is the smallest amount of catalyst used for this reaction in research reported to date. The CuO/MWCNT is chemically as well as physically very stable, heterogeneous in nature and reusable. After the catalytic reaction, MWCNTs were successfully separated from the used CuO/MWCNT and characterized by Raman, TEM and WAXD.