Ce-Containing MgAl-Layered Double Hydroxide-Graphene Oxide Hybrid Materials as Multifunctional Catalysts for Organic Transformations

The combination of layered double hydroxides (LDH) with graphene oxide (GO) enables the formation of nanohybrids with improved properties. This work focuses on the structural and catalytic properties of Ce-containing MgAl LDH-GO composites bearing different concentrations of GO in the range of 5–25 wt.%. The synthesis of the composites was performed by co-precipitating the LDH phase in the presence of GO, while their characterization was performed using XRF, XRD, DRIFT, Raman, SEM, nitrogen adsorption-desorption, and acidity-basicity measurements. The LDH-GO composites, showing redox, basic, and acid catalytic functions, were tested in two different types of organic transformations: (i) Knoevenagel condensation and (ii) one-pot cascade oxidation-Knoevenagel condensation. (i) The cinnamic acid was synthesized by the Knoevenagel condensation of benzaldehyde with diethylmalonate. The composites showed catalytic performances in strong contrast to neat LDH or GO, suggesting a synergistic interaction between the two components. During Knoevenagel condensation, the catalytic activity increased with the GO content in the hybrids up to 15 wt.% and decreased afterwards. (ii) 2-Benzoyl-3-phenylacrylonitrile was synthesized by the aerobic oxidation of benzyl alcohol followed by the Knoevenagel condensation with benzoyl acetonitrile using three different non-polar solvents, i.e., toluene, benzene, and mesitylene. The conversion of benzyl alcohol was higher for the hybrid materials compared to the individual components but decreased with the increase of the graphene oxide concentration.

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A Highly Efficient Bifunctional Catalyst CoOx/tri-g-C3N4 for One-Pot Aerobic Oxidation–Knoevenagel Condensation Reaction

Catalysts ◽

10.3390/catal10060712 ◽

2020 ◽

Vol 10 (6) ◽

pp. 712

Author(s):

Jiequn Wu ◽

Weiming Hua ◽

Yinghong Yue ◽

Zi Gao

Keyword(s):

Benzyl Alcohol ◽

Carbon Nitride ◽

Knoevenagel Condensation ◽

Condensation Reaction ◽

Aerobic Oxidation ◽

Product Yield ◽

Bifunctional Catalyst ◽

Catalytic Performance ◽

One Pot ◽

Highly Efficient

A highly efficient bifunctional catalyst of an s-triazine-based carbon-nitride-supported cobalt oxide is developed for the aerobic oxidation–Knoevenagel condensation tandem reaction of benzyl alcohol and malononitrile, whereby 96.4% benzyl alcohol conversion with nearly 100% selectivity towards benzylmalononitrile can be obtained in 6 h at 80 °C. The excellent catalytic performance derives from the high basicity of carbon nitride and strong redox ability of Co species induced by carbon nitride. The catalyst is also quite stable and can be reused without any regeneration treatment, whose product yield is only an 11.5% reduction after four runs.

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Ru(OH)x supported on polyethylenimine modified magnetic nanoparticles coated with silica as catalyst for one-pot tandem aerobic oxidation/Knoevenagel condensation of alcohols and active methylene compounds

Reaction Kinetics Mechanisms and Catalysis ◽

10.1007/s11144-018-1439-4 ◽

2018 ◽

Vol 125 (2) ◽

pp. 789-806 ◽

Cited By ~ 9

Author(s):

Huaipu Yan ◽

Hong-Yu Zhang ◽

Liping Wang ◽

Yuecheng Zhang ◽

Jiquan Zhao

Keyword(s):

Magnetic Nanoparticles ◽

Knoevenagel Condensation ◽

Aerobic Oxidation ◽

One Pot ◽

Active Methylene Compounds ◽

Modified Magnetic Nanoparticles ◽

Active Methylene

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Reduced graphene oxide supported palladium nanoparticles as an efficient catalyst for aerobic oxidation of benzyl alcohol

10.1063/5.0027427 ◽

2020 ◽

Author(s):

Hadeel Altaee ◽

Hassan A. Habeeb Alshamsi ◽

Baker A. Joda

Keyword(s):

Graphene Oxide ◽

Benzyl Alcohol ◽

Reduced Graphene Oxide ◽

Palladium Nanoparticles ◽

Aerobic Oxidation ◽

Efficient Catalyst ◽

Oxidation Of Benzyl Alcohol ◽

Reduced Graphene ◽

Supported Palladium

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Synergistic catalysis of Au–Cu/TiO2-NB nanopaper in aerobic oxidation of benzyl alcohol

Journal of Materials Chemistry A ◽

10.1039/c4ta01503g ◽

2014 ◽

Vol 2 (38) ◽

pp. 16292-16298 ◽

Cited By ~ 33

Author(s):

Qinqin Jia ◽

Dongfang Zhao ◽

Bin Tang ◽

Na Zhao ◽

Haidong Li ◽

...

Keyword(s):

Benzyl Alcohol ◽

Aerobic Oxidation ◽

Alcohol Oxidation ◽

Galvanic Replacement ◽

One Pot ◽

Benzyl Alcohol Oxidation ◽

Synergistic Catalysis ◽

Replacement Method ◽

Oxidation Of Benzyl Alcohol

The synergistic catalysis of Au–Cu/TiO2-NB nanostructure synthesized by one-pot photodeposition-galvanic replacement method in benzyl alcohol oxidation.

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Ru nanoparticles supported on N-doped reduced graphene oxide as valuable catalyst for the selective aerobic oxidation of benzyl alcohol

Catalysis Today ◽

10.1016/j.cattod.2019.05.057 ◽

2020 ◽

Vol 357 ◽

pp. 8-14 ◽

Cited By ~ 3

Author(s):

Carolina S. Ramirez-Barria ◽

Mark Isaacs ◽

Christopher Parlett ◽

Karen Wilson ◽

Antonio Guerrero-Ruiz ◽

...

Keyword(s):

Graphene Oxide ◽

Benzyl Alcohol ◽

Reduced Graphene Oxide ◽

Aerobic Oxidation ◽

Ru Nanoparticles ◽

Oxidation Of Benzyl Alcohol ◽

Reduced Graphene ◽

Selective Aerobic Oxidation

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One-pot Pseudo-Domino Three-Component Knoevenagel Condensation Reaction in Water Enabled by Micellar Catalyst: Mechanism and Reactivity

Letters in Organic Chemistry ◽

10.2174/1570178616666190701102542 ◽

2020 ◽

Vol 17 (11) ◽

pp. 823-831

Author(s):

Dini Ahanthem ◽

Devi Prasan Ojha ◽

Francis A.S. Chipem ◽

Warjeet S. Laitonjam

Keyword(s):

Knoevenagel Condensation ◽

Condensation Reaction ◽

Hydrophobic Effect ◽

Sodium Dodecyl ◽

Thiobarbituric Acid ◽

Aqueous Environment ◽

Organic Transformations ◽

One Pot ◽

Knoevenagel Condensation Reaction ◽

Electron Withdrawing Group

The micellar catalysis is well-known for its hydrophobic effect that is the tendency of nonpolar groups to cluster within the lipophilic core so as to shield them from contact with an aqueous environment formed upon the dissolution of a surfactant in water. This provides a unique opportunity to establish organic transformations in greener solvents, such as water leading to organic waste control and easy product isolation protocols. Considering the significant interaction of thiobarbituric acid moieties in a biological macromolecule core, herein, a highly efficient procedure for the synthesis of biological and medicinal important 5-(arylmethylene)dihydro-2-thioxo-4,6(1H,5H)-pyrimidinediones via Knoevenagel condensation of thiobarbituric acids and aldehydes catalyzed by a surfactant, sodium dodecyl sulfate, is developed. The synthetic procedure shows the excellent activity of the micellar catalysts towards the aldehyde activation leading to a facile condensation. The application of the method is demonstrated by further synthesis of 5,5'-(4-arylmethylene)bis[dihydro-2-thioxo-4,6(1H,5H)- pyrimidinediones]. Theoretical studies of the reaction were also carried out to investigate the effect of electron releasing and electron-withdrawing group in benzaldehyde on the reaction.

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A general one-pot synthetic strategy to reduced graphene oxide (rGO) and rGO-nanoparticle hybrid materials

Carbon ◽

10.1016/j.carbon.2018.10.087 ◽

2019 ◽

Vol 143 ◽

pp. 73-84 ◽

Cited By ~ 10

Author(s):

Rebecca F. Albers ◽

Rafael A. Bini ◽

João B. Souza ◽

Derik T. Machado ◽

Laudemir C. Varanda

Keyword(s):

Graphene Oxide ◽

Reduced Graphene Oxide ◽

Hybrid Materials ◽

One Pot ◽

Synthetic Strategy ◽

Reduced Graphene

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Versatile Post-functionalisation Strategy for the Formation of Modular Organic-Inorganic Polyoxometalate Hybrids

10.26434/chemrxiv-2021-lf03g ◽

2021 ◽

Author(s):

David E. Salazar Marcano ◽

Mhamad Aly Moussawi ◽

Alexander V. Anyushin ◽

Sarah Lentink ◽

Luc Van Meervelt ◽

...

Keyword(s):

Thermal Stability ◽

Hybrid Materials ◽

Large Family ◽

Building Blocks ◽

Hybrid Structures ◽

General Strategy ◽

One Pot ◽

Vis Spectroscopy ◽

The Individual ◽

Metal Oxo Clusters

Hybrid structures incorporating different organic and inorganic constituents are emerging as a very promising class of materials since they synergistically combine the complementary and diverse properties of the individual components. Hybrid materials based on polyoxometalates (POMs) are particularly interesting due to the versatile catalytic, redox, electronic, and magnetic properties of this large family of metal-oxo clusters, yet the combination of different clusters has been scarcely reported. Hence, herein we propose a novel and general strategy for combining multiple types of metal-oxo clusters in a single hybrid molecule. Two novel hybrid POM structures (HPOMs) bis-functionalised with dipentaerythritol (R-POM1-R; R = (OCH2)3CCH2OCH2C(CH2OH)) were synthesised as building-blocks for the formation of heterometallic hybrid triads (POM2-R-POM1-R-POM2). Such a modular approach resulted in the formation of four novel heterometallic hybrids combing the Lindqvist {V6}, Anderson-Evans {XMo6} (X = Cr or Al) and trisubstituted Wells-Dawson {P2V3W15} POM structures. Their formation was confirmed by multinuclear Nuclear Magnetic Resonance (NMR), infrared (IR) and UV-Vis spectroscopy, as well as Mass Spectrometry, Diffusion Ordered Spectroscopy (DOSY) and elemental analysis. Their thermal stability was also examined by Thermogravimetric Analysis (TGA), which showed that overall the HPOM triads exhibit higher thermal stability than comparable hybrid structures containing only one type of POM. The one-pot synthesis of these novel compounds was achieved in high yields in aqueous and organic media under simple reflux conditions, without the need of any additives, and could be applied for creating other hybrid materials based on a variety of metal-oxo cluster building-blocks.

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