Eco-friendly hydrogenation of aromatic aldehyde compounds by tandem dehydrogenation of dimethylamine-borane in the presence of a reduced graphene oxide furnished platinum nanocatalyst

Göksu, Haydar; Yıldız, Yunus; Çelik, Betül; Yazici, M Müge; Kılbaş, Benan; Sen, Fatih

doi:10.1039/c5cy01462j

Cited by 78 publications

(19 citation statements)

References 48 publications

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“…Also demonstrated by this technique are representative atomic lattice fringes. Finally, it was observed that the nominal range value of Pt (111) (0.228 nm) was in the same crystal range (0.228 nm) as the characterized Pt nanoparticle 31 .…”

Section: Resultsmentioning

confidence: 72%

Oxidation of Benzyl Alcohol Compounds in the Presence of Carbon Hybrid Supported Platinum Nanoparticles (Pt@CHs) in Oxygen Atmosphere

Göksu

Burhan

Mustafov

et al. 2020

Sci Rep

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A novel catalyst which carbon hybrid supported platinum nanoparticles were synthesized by our group for the oxidation of benzyl alcohol derivatives. In this study, this catalyst was utilized for the oxidation of benzyl alcohol derivatives to benzaldehyde compounds in aqueous toluene at 80 °C. The benzaldehyde derivatives were synthesized in high yields and mild conditions in the presence of the catalyst by the developed method. Additionally, the prepared nanoparticles have been characterized by Transmission Electron Microscopy (TEM), the high-resolution electron micrograph (HR-TEM), X-ray Photoelectron Spectroscopy (XPS), and X-ray Diffraction (XRD). The mean particle size of the nanoparticles determined by the XRD technique was found to be 2.83 nm in parallel with TEM analysis. TEM analysis also indicated that the Pt nanoparticles were evenly dispersed on the support material. Finally, the Pt@CHs catalyst was shown also stable and reusable for the oxidation reaction, providing ≤95% conversion after its 3rd consecutive use in the oxidation reaction of various compounds.

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Section: Resultsmentioning

confidence: 72%

Oxidation of Benzyl Alcohol Compounds in the Presence of Carbon Hybrid Supported Platinum Nanoparticles (Pt@CHs) in Oxygen Atmosphere

Göksu

Burhan

Mustafov

et al. 2020

Sci Rep

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“…As a reference, the C 1s peak was used at 286.4 eV and the correct binding energy was determined (± 0.3 eV) in all XPS spectra of the prepared materials. 39,40…”

Section: Resultsmentioning

confidence: 99%

“…The shift of the binding energy of nickel to the 2p 3/2 peak indicates the alloying of nickel with palladium at a low energy. 39,40…”

Section: Resultsmentioning

confidence: 99%

Composites of Palladium–Nickel Alloy Nanoparticles and Graphene Oxide for the Knoevenagel Condensation of Aldehydes with Malononitrile

et al. 2019

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Herein, we have described uniformly dispersed palladium–nickel nanoparticles furnished on graphene oxide (GO-supported PdNi nanoparticles) as a powerful heterogeneous nanocatalyst for the promotion of Knoevenagel reaction between malononitrile and aromatic aldehydes under mild reaction conditions. The successful characterization of PdNi nanoparticles on the GO surface was shown by X-ray diffraction, X-ray photoelectron spectroscopy, high-resolution transmission electron microscopy (HR-TEM), and TEM. GO-supported PdNi nanoparticles, which are used as highly efficient, stable, and durable catalysts, were used for the first time for the Knoevenagel condensation reaction. The data obtained here showed that the GO-supported PdNi nanocatalyst had a unique catalytic activity and demonstrated that it could be reused five times without a significant decrease in the catalytic performance. The use of this nanocatalyst results in a very short reaction time under mild reaction conditions, high recyclability, excellent catalytic activity, and a straightforward work-up procedure for Knoevenagel condensation of malononitrile and aromatic aldehydes.

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“…2-(2-Furanylmethylene) malononitrile (26) was obtained in quantitative yields and in a short time using furan-2-carbaldehyde (25), which is heteroaromatic aldehyde (Table 2, entry 13). On the other hand, this reaction was carried out with aliphatic aldehydes to compare with aromatic aldehydes.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of benzylidenemalononitrile by Knoevenagel condensation through monodisperse carbon nanotube-based NiCu nanohybrids

Zengin

Burhan

Şavk

et al. 2020

Sci Rep

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Monodisperse nickel/copper nanohybrids (nicu@MWcnt) based on multi-walled carbon nanotubes (MWcnt) were prepared for the Knoevenagel condensation of aryl and aliphatic aldehydes. the synthesis of these nanohybrids was carried out by the ultrasonic hydroxide assisted reduction method. nicu@MWcnt nanohybrids were characterized by analytical techniques such as X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), transmission electron microscopy (teM), high-resolution transmission electron microscopy (HR-teM), and Raman spectroscopy. According to characterization results, nicu@MWcnt showed that these nanohybrids form highly uniform, crystalline, monodisperse, colloidally stable nicu@MWcnt nanohybrids were successfully synthesized. thereafter, a model reaction was carried out to obtain benzylidenemalononitrile derivatives using nicu@MWcnt as a catalyst, and showed high catalytic performance under mild conditions over 10-180 min. Benzylidenemalononitrile (BMN) derivatives are frequently used as both a target molecule and an intermediate molecule in organic chemistry. BMN derivatives have attracted many scientists' attention because of some unique properties such as anticancer 1-3 , antifungal 4,5 , antibacterial 6-9 , anti-corrosive 10. BMN derivatives are used to increase cell resistance in the case of oxidative stress 11 , in prostaglandin biosynthesis 12 , in the design of photoconductive cells 13 and the inhibition/activation of certain enzymes 14,15. Typically, BMN derivatives are synthesized by the Knoevenagel condensation of aldehydes with active methylene compounds (Fig. 1) 16-22. In these processes, it is seen that it has an effect on homogeneous catalysts. Heterogeneous catalysts have various advantages such as minimum availability, recovery, reusability, structural deterioration resistance and leaching of metal values 23-28. Bimetallic heterogeneous catalysts, in particular, have greatly facilitated the Knoevenagel condensation reaction 29-34. In literature, many catalysts such as SBA-15 (highly stable mesoporous silica) 35 , Sr 3 Al 2 O 6 nanoparticles 36 , bifunctional MIL-101(Cr) 37 , Fe 3 O 4 @SiO 2 nanoparticles 38 and Mn-MOF@Pi 39 have been used in condensation reactions. Herein we report an eco-friendly and practical method for the synthesis of highly efficient, cost-effective, and monodisperse bimetallic NiCu@MWCNT nanohybrids for the Knoevenagel condensation reaction under mild conditions. BMN derivatives have been successfully obtained in a very short time (10-180 min) using the developed method in the water-containing solvent system. experimental chemicals. NiCl 2 , CuCl 2 , NaBH 4 , aminoborane aryl azides, acetonitrile (ACN), lithium perchlorate (LiClO 4), 3,4-ethylene dioxythiophene (EDOT), multiwall carbon nanotubes, NN-Dimethylformamide (DMF), sulfuric acid, hydrochloric acid, and nitric acid were purchased from Sigma-Aldrich. Tetrahydrofuran (THF; 99.5%), HClO 4 (60%), 2-propanol, and Methanol (≥ 99.5%) were obtained from Merck. All test materials and other

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Eco-friendly hydrogenation of aromatic aldehyde compounds by tandem dehydrogenation of dimethylamine-borane in the presence of a reduced graphene oxide furnished platinum nanocatalyst

Abstract: An easy and effective synthetic method has been developed for the reduction of aldehyde compounds in the presence of monodisperse Pt(0)/TPA@rGO NPs as the catalyst.

Cited by 78 publications

References 48 publications

Oxidation of Benzyl Alcohol Compounds in the Presence of Carbon Hybrid Supported Platinum Nanoparticles (Pt@CHs) in Oxygen Atmosphere

Oxidation of Benzyl Alcohol Compounds in the Presence of Carbon Hybrid Supported Platinum Nanoparticles (Pt@CHs) in Oxygen Atmosphere

Composites of Palladium–Nickel Alloy Nanoparticles and Graphene Oxide for the Knoevenagel Condensation of Aldehydes with Malononitrile

Synthesis of benzylidenemalononitrile by Knoevenagel condensation through monodisperse carbon nanotube-based NiCu nanohybrids

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