Copper(I) Confined in Interlayer Space of Montmorillonite: A Highly Efficient and Recyclable Catalyst for Click Reaction

Mekhzoum, Mohamed El Mehdi; Benzeid, Hanane; Qaiss, Abou el kacem; Essassi, El Mokhtar; Bouhfid, Rachid

doi:10.1007/s10562-015-1625-1

Cited by 31 publications

(17 citation statements)

References 37 publications

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“…Another instance of a copper-exchanged clay material, in this case natural montmorillonite, was described recently by Mekhzoum et al [204]. Rather surprisingly in view of the very low solubility of CuI in water (approximate 4.2 × 10 −4 M at 18–20 °C) [205], the material was reportedly prepared by vigorous stirring of the clay in a saturated aqueous solution of the copper salt.…”

Section: Cu-exchanged Clays and Other Inorganic Materialsmentioning

confidence: 99%

Recent Advances in Recoverable Systems for the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction (CuAAC)

Mandoli

2016

Molecules

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Abstract:The explosively-growing applications of the Cu-catalyzed Huisgen 1,3-dipolar cycloaddition reaction between organic azides and alkynes (CuAAC) have stimulated an impressive number of reports, in the last years, focusing on recoverable variants of the homogeneous or quasi-homogeneous catalysts. Recent advances in the field are reviewed, with particular emphasis on systems immobilized onto polymeric organic or inorganic supports.

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Section: Cu-exchanged Clays and Other Inorganic Materialsmentioning

confidence: 99%

Recent Advances in Recoverable Systems for the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction (CuAAC)

Mandoli

2016

Molecules

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“…It is worth mentioning that the results showed alkyl and aryl halides react better than haloketones in terms of yields and reaction times. The efficiency of CuI@[PMMA‐co‐MI] in click reaction was also compared with that of previously reported catalysts under various reaction conditions (Table ) . By comparison, it can be concluded that CuI@[PMMA‐co‐MI] as a novel nanocatalyst has several merits such as higher or comparable yield of the desired product in shorter reaction time.…”

Section: Resultsmentioning

confidence: 95%

In situpreparation and characterization of novel CuI‐functionalized poly[(methyl methacrylate)‐co‐maleimide] as an efficient heterogeneous catalyst in the regioselective synthesis of 1,2,3‐triazoles via click reaction: Experimental and computational chemistry

Pourmohammad

Heravi

Ahmadi

et al. 2019

Applied Organom Chemis

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A CuI‐functionalized poly[(methyl methacrylate)‐co‐maleimide] (CuI@[PMMA‐co‐MI]) nanocatalyst was prepared from in situ polymerization and functionalization of poly[(methyl methacrylate)‐co‐(maleic anhydride)] and well characterized using various techniques. From a computational viewpoint, we assessed two complexation models between copper nanoparticles and [PMMA‐co‐MI]. In this line, the metal–ligand interaction strength was also studied via density functional theory calculations and frontier molecular orbital analysis. Moreover, for presenting a quantitative description of the electronic features of immobilization of copper nanoparticles on polymeric support, the topological analysis of electron density and its Laplacian was performed through quantum theory of atoms in molecules. Finally, the catalytic activity of CuI@[PMMA‐co‐MI] as a heterogeneous nanocatalyst was successfully examined in the highly regioselective synthesis of 1,4‐disubstituted 1,2,3‐triazoles via click reaction.

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“…Finally, the efficiency of CuI@HNTs‐2 N‐Sal for the above‐mentioned click reaction was compared with that of some previously reported catalysts under various reaction conditions (Table ) . Comparing the protocols, it can be concluded that use of CuI@HNTs‐2 N‐Sal led to higher or comparable yield of the desired product in shorter short reaction time.…”

Section: Resultsmentioning

confidence: 97%

CuI‐functionalized halloysite nanoclay as an efficient heterogeneous catalyst for promoting click reactions: Combination of experimental and computational chemistry

Bahri‐Laleh

Sadjadi

Heravi

et al. 2018

Applied Organom Chemis

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Amine-functionalized halloysite nanotubes (HNTs-2 N) were prepared and further modified by introduction of salicylaldehyde and formation of imine functionality (HNTs-2 N-Sal). The latter was subsequently used for immobilization of CuI and formation of CuI@HNTs-2 N-Sal, which could effectively promote click reactions of terminal alkynes, sodium azide and α-haloketones or alkyl halides in aqueous media and under mild reaction conditions to afford 1,2,3-triazoles in relatively short reaction times. Notably, the catalyst could be recycled in up to six reaction runs with negligible loss of catalytic activity and CuI leaching. Also, the geometry of CuI adsorption on the modified HNTs surface was explored by molecular simulation with density functional theory. Furthermore, topographic steric maps of possible coordination modes were obtained using the recently released SambVca2 web application tool. Based on obtained results, a catalytic site with superior performance was suggested.

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Copper(I) Confined in Interlayer Space of Montmorillonite: A Highly Efficient and Recyclable Catalyst for Click Reaction

Cited by 31 publications

References 37 publications

Recent Advances in Recoverable Systems for the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction (CuAAC)

Recent Advances in Recoverable Systems for the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction (CuAAC)

In situpreparation and characterization of novel CuI‐functionalized poly[(methyl methacrylate)‐co‐maleimide] as an efficient heterogeneous catalyst in the regioselective synthesis of 1,2,3‐triazoles via click reaction: Experimental and computational chemistry

CuI‐functionalized halloysite nanoclay as an efficient heterogeneous catalyst for promoting click reactions: Combination of experimental and computational chemistry

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