Reduced zwitterionic graphene oxide sheets decorated with nickel nanoparticles as magnetically and efficient catalyst for A3‐coupling reactions under optimized green experimental conditions

A Ni‐based supported reduced zwitterionic graphene oxide N,N‐bis(2‐pyridylmethyl)ethylenediamine 1,3‐propanesultone (GO‐BPED‐PS) material was prepared for the catalysis of A3‐coupling reactions under green experimental conditions. First, the in situ generation of nickel nanoparticles (NiNPs) onto th...

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Bibliographic Details
Published in:Applied organometallic chemistry 2022-06, Vol.36 (6), p.n/a
Main Authors: Chaabane, Laroussi, Baouab, Mohamed Hassen V., Beyou, Emmanuel
Format: Article
Language:English
Subjects:
A3‐coupling reaction
Alkynes
Benzaldehyde
Catalysis
Catalysts
Catalytic activity
Chemical reactions
Chemistry
Coupling
Crystallography
Electron density
Ethylenediamine
Graphene
green solvent
Infrared analysis
Nanoparticles
Nickel
nickel nanoparticles
Reaction time
Sheets
Thermogravimetric analysis
zwitterionic graphene oxide
Zwitterions
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Summary:A Ni‐based supported reduced zwitterionic graphene oxide N,N‐bis(2‐pyridylmethyl)ethylenediamine 1,3‐propanesultone (GO‐BPED‐PS) material was prepared for the catalysis of A3‐coupling reactions under green experimental conditions. First, the in situ generation of nickel nanoparticles (NiNPs) onto the reduced zwitterionic GO‐BPED‐PS sheets was characterized by various techniques such as Fourier infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), X‐ray diffraction (XRD), scanning electron microscopy (SEM), and vibrating sample magnetometer (VSM) analysis. Moreover, the electron density map of NiNPs onto the reduced zwitterionic GO‐based sheets was produced through the X‐ray crystallographic analysis. Then, the as‐prepared reduced GO‐BPED‐PS NiNPs (rGO‐BPED‐PS@NiNPs) material was used as a heterogeneous catalyst for the three‐component coupling reaction (A3‐coupling reaction) of benzaldehyde, morpholine, and terminal alkynes. The experimental conditions were performed in order to obtain very good green chemistry metrics. In particular, we obtained a high catalytic efficiency when using γ‐valerolactone as solvent, a reaction time of 3 h and a temperature of 100°C. In addition, it was demonstrated that the rGO‐BPED‐PS@NiNPs catalyst could be recycled for 11 times without a significant decrease in its catalytic activity. The heterogeneous catalyst rGO‐BPED‐PS@NiNPs was prepared through in situ generation of nickel nanoparticles (NiNPs) onto the reduced zwitterionic GO‐BPED‐PS sheets. Then, it was used as a supported catalyst for a three‐component coupling reaction involving benzaldehyde, morpholine, and a series of terminal alkynes in γ‐valerolactone as a green solvent. Furthermore, this magnetic rGO‐BPED‐PS@NiNPs catalyst was effectively reused up to 11 runs without a significant loss in its catalytic activity and exhibited very good green chemistry metrics.
ISSN:0268-2605
1099-0739
DOI:10.1002/aoc.6625