Cobalt nanoparticles supported on ionic liquid‐functionalized multiwall carbon nanotubes as an efficient and recyclable catalyst for Heck reaction

Hajipour, Abdol R.; Khorsandi, Zahra; Karimi, Hirbod

doi:10.1002/aoc.3372

Cited by 33 publications

(14 citation statements)

References 77 publications

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“…14 Lauer and co-workers recently reported conditions for achieving excellent vinyl selectivity in the Heck coupling of cyclic olefins with aryl bromides using neopentyl phosphine ligands. In continuation of our recent investigations on the application of heterogeneous catalytic systems in cross-coupling reactions; [56][57][58][59][60] In this report, palladium is supported on the ss-DNA-functionalized MWCNTs materials to give a new and highly stable palladium catalyst (Pd/DNA@MWCNTs). Moreover, in concern to toxicity of palladium residuals, acceptable limits of palladium traces in pharmaceuticals were set usually as ppm level.…”

Section: Introductionmentioning

confidence: 78%

Regioselective Heck reaction catalyzed by Pd nanoparticles immobilized on DNA-modified MWCNTs

2016

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This is the first report of regioselective Heck reaction of aryl iodides with 2,3-dihydrofuran using heterogonous nanocatalyst. Herein, palladium nanoparticles is immobilized on DNA-modified multi walled carbon nanotubes and characterized by FT-IR spectroscopy, UV-vis spectroscopy, field emission scanning electron microscopy, X-ray diffraction, transmission electron microscopy, inductively coupled plasma and elemental analysis. DNA as a welldefined structure and biodegradable natural polymer generate the palladium catalyst which showed high activity in common and regioselective Heck reaction in excellent yields and good selectivity under ligand-free and mild reaction conditions. Moreover, the catalyst could be recovered and reused at least nine times without any considerable loss of its catalytic activity.

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Section: Introductionmentioning

confidence: 78%

Regioselective Heck reaction catalyzed by Pd nanoparticles immobilized on DNA-modified MWCNTs

2016

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“…If we look at Table , the results are evidence of this fact. Although aryl chloride reacted for a long time and with low efficiency, but, it should be taken into account that many reported cobalt catalytic systems showed no activity with aryl chloride substrates in the Mizoroki–Heck reaction . The high performance of this bio‐catalyst can be attributed to synergistic good effects of cobalt nanoparticles with ligand which grafted on MNP and good dispersion of cobalt nanoparticles.…”

Section: Resultsmentioning

confidence: 94%

“…Cobalt catalysts are a very good choice owing to their higher catalytic activities, nontoxicity, low‐cost, chemical and mechanical stability, and availability . Accordingly, to improve the Heck–Mizoroki and the Suzuki–Miyaura cross‐coupling reactions, a number of important studie have utilized new catalytic systems based on cobalt . Development of functional groups on supports such as –SO 3 H, –COOH, –NH 2 , –CONH 2 , and –OH for immobilization of metallic nanoparticles is yet another challenge.…”

Section: Introductionmentioning

confidence: 99%

Magnetic apple seed starch functionalized with 2,2′‐furil as a green host for cobalt nanoparticles: Highly active and reusable catalyst for Mizoroki–Heck and the Suzuki–Miyaura reactions

Arghan

Koukabi

Kolvari

2019

Applied Organom Chemis

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From the perspective of green chemistry, in catalytic systems, being low cost and eco‐friendly, in addition to high chemical and thermal stability, are requirements of support materials. In this regard, we used apple seed starch as an accessible, nontoxic, and cost‐effective support material. In order to take advantage of magnetic separation, the magnetite nanoparticles were chosen as an ideal pair for apple seed starch. Furthermore, during the Schiff base reaction, the magnetic apple seed starch was functionalized with 2,2′‐furil along with amine functionality to be used as a bio‐support for immobilization of cobalt. The introduction of cobalt had a significant effect on the greenness of the catalyst and reducing its price. FT‐IR, TGA, XRD, FE‐SEM, TEM, VSM, ninhydrin test, element mapping, AAS, and EDX analysis were applied to characterize the newly prepared catalyst. The effectiveness of this novel Schiff base supported catalyst was evaluated in the Mizoroki–Heck and the Suzuki–Miyaura coupling reactions. High reactivity and selectivity were among the most prominent characteristics of the catalyst as compared to previously reported catalysts. The longevity test and hot filtration showed the ability to use the catalyst at least 5 times and negligible cobalt leaching during the reaction, respectively. This work is the first report on the usage of apple seed starch as a supporting catalyst and 2,2′‐furil as a ligand in the catalyst modifications and catalytic activity. Accordingly, this can be the beginning of an attractive way in the design and synthesis of heterogeneous catalysts.

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“…[49][50][51] The high activity of MNP@PAMAM-Co is probably due to good dispersion of cobalt nanoparticles and good synergistic effects of cobalt nanoparticles with ligands that are grafted on MNP. The first step of this catalytic coupling reaction is oxidative addition, so the reactivity of C-halogen bond has definite influence.…”

Section: Performance Of the Catalyst On Several Substrates For Mizomentioning

confidence: 99%

Cobalt supported on dendronized magnetic nanoparticles: A new highly efficient and recyclable catalyst for the Mizoroki–Heck cross‐coupling reaction

Arghan

Koukabi

Kolvari

2019

Applied Organom Chemis

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Funding information Semnan UniversityPolyamidoamine (PAMAM) is one of the most interesting types of hyperbranched polymers that carry a large number of amino groups on its surface. PAMAM has gained significant attention from synthetic organic chemists due to its structural characteristics, controllable structure, inner porosity, and ability to trap a wide range of ions and molecules. So, in this work, the PAMAM dendrimer was synthesized, grafted onto the surface of magnetite nanoparticles, and the resulting hybrid nanoparticles were then employed as suitable host for immobilizing cobalt nanoparticles. The newly developed catalyst was well characterized by Fourier transform-infrared, X-ray diffraction, thermogravimetric analysis, field emission-scanning electron microscopy, transmission electron microscopy, atomic absorption spectroscopy, element mapping and energy-dispersive X-ray analysis. The efficiency of the as-prepared nanocatalyst was evaluated for the Mizoroki-Heck crosscoupling reactions. The MNP@PAMAM-Co represented perfect catalytic efficiency and high selectivity for the Mizoroki-Heck cross-coupling reaction compared with previously reported catalysts. The catalyst separation from the reaction mixture was easily achieved with the assistance of an external magnetic field, and its recycling was also investigated for five consecutive runs. Hot filtration confirmed no leaching of the active metal during the Heck coupling.

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Cobalt nanoparticles supported on ionic liquid‐functionalized multiwall carbon nanotubes as an efficient and recyclable catalyst for Heck reaction

Cited by 33 publications

References 77 publications

Regioselective Heck reaction catalyzed by Pd nanoparticles immobilized on DNA-modified MWCNTs

Regioselective Heck reaction catalyzed by Pd nanoparticles immobilized on DNA-modified MWCNTs

Magnetic apple seed starch functionalized with 2,2′‐furil as a green host for cobalt nanoparticles: Highly active and reusable catalyst for Mizoroki–Heck and the Suzuki–Miyaura reactions

Cobalt supported on dendronized magnetic nanoparticles: A new highly efficient and recyclable catalyst for the Mizoroki–Heck cross‐coupling reaction

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