Synthesis and crystal structures of a series of (μ-thiophenolato)(μ-pyrazolato-N,N′) double bridged dipalladium(II) complexes and their application in Mizoroki–Heck reaction as highly efficient catalysts

Khadir, Narjes; Tavakoli, Ghazal; Assoud, Abdeljalil; Bagherzadeh, Mojtaba; Boghaei, Davar M.

doi:10.1016/j.ica.2015.10.035

Cited by 11 publications

(3 citation statements)

References 60 publications

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“…In organic chemistry, a large number of reviews have been published covering Heck–Mizoroki and Suzuki–Miyaura C–C cross‐coupling reactions as they are the most fundamental reactions in organic synthesis owing to their application in the synthesis of natural products, numerous drugs, biologically active compounds, and many organic building blocks . Principally, palladium catalysts are used to activate aryl halides for the Heck–Mizoroki and the Suzuki–Miyaura cross‐coupling reactions. Although palladium catalysts are uncompetitive in synthetic versatility, they suffer from disadvantages such as high cost, air sensitivity, and toxicity of complexes, all of which limit their use in the industry.…”

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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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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“…The Mizoroki-Heck reaction is the palladium catalyzed carbon-carbon bond formation between aryl halides and olefins is known to employ significant roles in modern synthetic chemistry [1,2] and are used extensively for agrochemical industry, pharmaceutical intermediates, conducting polymers, pesticides and liquid crystals application [3][4][5]. Basically, Mizoroki-Heck reaction is carried out in an organic solvent, such as amine, benzene, toluene, N,N-dimethylacetamide, N,N-dimethylformamide or tetrahydrofuran, which could give excellent performance and conversion to the catalytic product due to the solubility of most organic compound in N,N-dimethyl acetamide [6,7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Catalytic Applications of 2,2-Dimethylpropane-1,3-Diaminopalladium(II) Complex in Mizoroki-Heck Reaction

Soh

Shamsuddin

2017

Asian J. Chem.

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New tetradentate Schiff base ligand (LSB) and its palladium(II) complex, i.e., complexation of N,N'-bis(4-methoxysalicylidene)-2,2-dimethylpropane-1,3-diaminopalladium(II) (PdLSB) has been successfully synthesized through condensation reaction between primary amine 2,2-dimethyl-1,3-propanediamine with 2-hydroxy-4-methoxybenzaldehyde. The palladium complex was then prepared by refluxing the corresponding LSB with an equimolar amount of palladium(II) acetate to give C21H24N2O4Pd. The complex was characterized by using several techniques, such as the elemental chemical analysis CHN, FTIR, NMR spectroscopy and single crystal X-ray crystallography. This air/moisture stable complex was investigated to be a high class of homogeneous catalyst for Mizoroki-Heck reaction. The reaction was monitored by GC-FID at 12 h reaction period. The percentage conversion of 4-bromoacetophenone was 70 % indicated that PdLSB can act as an ideal potential catalyst in the Mizoroki-Heck reaction.

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“…To catalyse a large variety of carbon–carbon bond forming reactions, palladium is one of the most essential transition metals which is commonly used . Various kinds of cross‐coupling reactions have been investigated; among them coupling reactions such as the Heck–Mizoroki reaction, the Suzuki reaction, the Sonogashira reaction, the Kumada reaction, the Negishi reaction and the Stille reaction are interesting examples of C;C bond formation…”

Section: Introductionmentioning

confidence: 99%

Nano tetraimine Pd(0) complex as an efficient catalyst for phosphine‐free Suzuki reaction in water and copper‐free Sonogashira reaction under aerobic conditions

Mandegani

Asadi

2016

Applied Organom Chemis

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A nano tetraimine Pd(0) complex catalyst was successfully used as an efficient heterogeneous catalyst for the phosphine‐free palladium‐catalysed Suzuki coupling reaction in water at 80 °C. This nano tetraimine Pd(0) complex was also used for copper‐free Sonogashira reaction in dimethylformamide at 100 °C. The catalyst was easily recovered from the reaction mixture by centrifugation and reused for at least six cycles without any significant loss in its catalytic activity. Analysis of the reaction mixture using inductively coupled plasma analysis showed that leaching of palladium from the catalyst was negligible. The reactions can be performed efficiently for aryl iodides, bromides and also chlorides. Copyright © 2016 John Wiley & Sons, Ltd.

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Synthesis and crystal structures of a series of (μ-thiophenolato)(μ-pyrazolato-N,N′) double bridged dipalladium(II) complexes and their application in Mizoroki–Heck reaction as highly efficient catalysts

Cited by 11 publications

References 60 publications

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

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

Synthesis, Characterization and Catalytic Applications of 2,2-Dimethylpropane-1,3-Diaminopalladium(II) Complex in Mizoroki-Heck Reaction

Nano tetraimine Pd(0) complex as an efficient catalyst for phosphine‐free Suzuki reaction in water and copper‐free Sonogashira reaction under aerobic conditions

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