Synthesis of magnetically recyclable Fe3O4@[(EtO)3Si–L1H]/Pd(II) nanocatalyst and application in Suzuki and Heck coupling reactions

Keypour, Hassan; Saremi, Shokoufeh Ghahri; Noroozi, Mohammad; Veisi, Hojat

doi:10.1002/aoc.3558

Cited by 26 publications

(13 citation statements)

References 43 publications

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“…[18,20,21] Incorporation of MNPs within the channels of SBA-15 leads to the formation of Fe x O y @SBA-15 particles that can be employed as magnetically retrievable catalyst supports. [26] Though mesoporous silica composites have been widely applied to coupling reactions, limited studies have been reported about anchoring homogeneous catalysts on mesoporous magnetic silica for C-C coupling reactions. Their porous magnetic nanocomposites showed high activity towards esterification of propionic acid, in addition to facile recovery and re-use.…”

Section: Introductionmentioning

confidence: 99%

“…Their supported catalyst was used in the Suzuki cross-coupling reaction of various aryl halides (I, Br, and Cl) with phenylboronic acid and in the Heck coupling reaction of aryl halides (I and Br) with styrene. [26] Though mesoporous silica composites have been widely applied to coupling reactions, limited studies have been reported about anchoring homogeneous catalysts on mesoporous magnetic silica for C-C coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

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N‐heterocyclic carbene–palladium(II) complex supported on magnetic mesoporous silica for Heck cross‐coupling reaction

Nuri

Mansoori

Bezaatpour

2019

Applied Organom Chemis

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Magnetic mesoporous silica was prepared via embedding magnetite nanoparticles between channels of mesoporous silica (SBA-15). The prepared composite (Fe 3 O 4 @SiO 2 -SBA) was then reacted with 3-chloropropyltriethoxysilane, sodium imidazolide and 2-bromopyridine to give 3-(pyridin-2-yl)-1Himidazol-3-iumpropyl-functionalized Fe 3 O 4 @SiO 2 -SBA as a supported pincer ligand for Pd(II). The functionalized magnetic mesoporous silica was further reacted with [PdCl 2 (SMe 2 ) 2 ] to produce a supported N-heterocyclic carbene-Pd(II) complex. The obtained catalyst was characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, energy-dispersive X-ray analysis, vibrating sample magnetometry, Brunauer-Emmett-Teller surface area measurement and X-ray diffraction. The amount of the loaded complex was 80.3 mg g −1 , as calculated through thermogravimetric analysis. The formation of the ordered mesoporous structure of SBA-15 was confirmed using low-angle X-ray diffraction and transmission electron microscopy. Also, X-ray photoelectron spectroscopy confirmed the presence of the Pd(II) complex on the magnetic support. The prepared magnetic catalyst was then effectively used in the coupling reaction of olefins with aryl halides, i.e. the Heck reaction, in the presence of a base. The reaction parameters, such as solvent, base, temperature, amount of catalyst and reactant ratio, were optimized by choosing the coupling reaction of 1-bromonaphthalene and styrene as a model Heck reaction. N-Methylpyrrolidone as solvent, 0.25 mol% catalyst, K 2 CO 3 as base, reaction temperature of 120°C and ultrasonication of the catalyst for 10 min before use provided the best conditions for the Heck cross-coupling reaction. The best results were observed for aryl bromides and iodides while aryl chlorides were found to be less reactive. The catalyst exhibited noticeable stability and reusability.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

N‐heterocyclic carbene–palladium(II) complex supported on magnetic mesoporous silica for Heck cross‐coupling reaction

Nuri

Mansoori

Bezaatpour

2019

Applied Organom Chemis

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“…synthesized a Pd(II) Schiff base complex supported on magnetite nanoparticles as a retrievable heterogeneous catalyst. The supported catalyst was used in Suzuki cross‐coupling reaction of various aryl halides (I, Br, Cl) with phenylboronic acid and Heck coupling reaction of aryl halides (I, Br) with styrene …”

Section: Introductionmentioning

confidence: 99%

Magnetic Mesoporous SBA‐15 Functionalized with a NHC Pd(II) Complex: An Efficient and Recoverable Nanocatalyst for Hiyama Reaction

et al. 2019

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Magnetite nanoparticles (MNPs) were covered by a silica shell and then embedded into mesoporous silica . Magnetic mesoporous silica (Fe 3 O 4 @SiO 2 -SBA) was then reacted with 3chloropropyltriethoxysilane (CPTS), sodium salt of imidazole and 2-bromopyridine to give Fe 3 O 4 @SiO 2 -SBA functionalized with 3-(pyridin-2-yl)-1H-imidazol-3-ium-propyl (PIP) as a supported pincer ligand for Pd(II). The functionalized magnetic mesoporous silica were then treated with t-BuOK at À 80°C in THF and then reacted with [PdCl 2 (SMe 2 ) 2 ] to give supported Pd (II)-carbene complex containing C,N-bidentate ligand. The chloride ions were then exchanged by bromide ions using a NaBr solution of diethylether/acetone mixture. The prepared catalyst was characterized with, FT-IR, thermo gravimetric analysis (TGA), scanning electron microscopy (SEM), transmission electron microscopy (TEM), vibrating sample magnetometry (VSM), Brunauer-Emmett-Teller surface area measurement (S BET ), energy dispersive X-ray analysis (EDX) and wide angle X-ray diffraction spectroscopy (XRD). The prepared magnetic catalyst was effectively used in the coupling reaction of triethoxyphenylsilane with aryl halides (Hiyama reaction) in the presence of a base. The reaction parameters such as solvents, amount of catalyst, base and temperature were optimized. The catalyst was then magnetically decanted, washed, and reused several times.

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“…From this point of view, heterogeneous Pd catalytic systems are preferred for industrial applications because of their easy recovery and separation from reaction systems . Consequently, immobilization of Pd catalysts on supports such as polymers, silica, carbon and metal oxides has been extensively investigated in Suzuki–Miyaura reactions. However, some of these heterogeneous Pd catalysts have a lower activity in comparison with their counterpart homogeneous systems …”

Section: Introductionmentioning

confidence: 99%

Porphyrin‐based polymer‐supported palladium as an excellent and recyclable catalyst for Suzuki–Miyaura coupling reaction in water

Chen

Zhang

Zhu

et al. 2017

Applied Organom Chemis

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A porphyrin‐based polymer with high surface area was synthesized using 5,10,15,20‐tetraphenylporphyrin through a one‐pot Friedel–Crafts alkylation reaction. Pd(II) was successfully supported on this polymer. This strategy provides an easy approach to produce highly stable Pd–porphyrin‐based polymer. The resulting Pd catalyst was characterized using Fourier transform infrared and X‐ray photoelectron spectroscopies, thermogravimetric analysis, scanning and transmission electron microscopies and N2 adsorption–desorption measurements. This porphyrin‐based polymer‐supported Pd was used as a heterogeneous catalyst for Suzuki–Miyaura coupling reaction in water. The results demonstrated that this Pd catalyst indeed exhibited excellent catalytic activity and recycling performance in water, even for inactive aryl chloride substrate. A new heterogeneous strategy for catalyzing the Suzuki–Miyaura reaction in water is provided.

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Synthesis of magnetically recyclable Fe₃O₄@[(EtO)₃Si–L¹H]/Pd(II) nanocatalyst and application in Suzuki and Heck coupling reactions

Cited by 26 publications

References 43 publications

N‐heterocyclic carbene–palladium(II) complex supported on magnetic mesoporous silica for Heck cross‐coupling reaction

N‐heterocyclic carbene–palladium(II) complex supported on magnetic mesoporous silica for Heck cross‐coupling reaction

Magnetic Mesoporous SBA‐15 Functionalized with a NHC Pd(II) Complex: An Efficient and Recoverable Nanocatalyst for Hiyama Reaction

Porphyrin‐based polymer‐supported palladium as an excellent and recyclable catalyst for Suzuki–Miyaura coupling reaction in water

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