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Relevant academic research and scientific papers

Fe3O4@SiO2-polymer-imid-Pd magnetic porous nanosphere as magnetically separable catalyst for Mizoroki-Heck and Suzuki-Miyaura coupling reactions

The activity of palladium nanoparticles supported on poly (N-vinylpyrrolidone) grafted Fe3O4@SiO2 was investigated in the cross-coupling reactions. We have applied this catalyst under low loading of the supported palladium nanoparticles for the coupling of aryl halides with alkenes (Mizoroki-Heck reaction) and organoboronic acids (Suzuki-Miyaura reaction) in the absence of phosphorous ligands. Short reaction times and excellent yields of the products express the effectiveness of this catalyst. The nanocatalyst can be separated from the reaction mixture by applying a permanent magnet externally and can be reused for six times without appreciable change in catalytic activity. Also, the amount of leaching of Pd nanoparticles has been determined by ICP analysis and results showed low leaching of the metal into solution from the supported catalyst.

Air-Stable Fe3O4@SiO2-EDTA-Ni(0) as an Efficient Recyclable Magnetic Nanocatalyst for Effective Suzuki-Miyaura and Heck Cross-Coupling via Aryl Sulfamates and Carbamates

The synthesis of inexpensive and novel air-stable Ni(0) nanoparticles immobilized on the EDTA-modified Fe3O4@SiO2 nanocatalyst was investigated in Suzuki-Miyaura and Heck cross-coupling reactions. This catalytic system displayed a greatly improved substrate scope for the carbon–carbon bond formations starting from a wide range of green and economical electrophiles aryl and heteroaryl carbamates and sulfamates via highly efficient method under mild, operationally simple reaction conditions. The synthesized heterogeneous catalyst was also fully characterized by FT-IR, TEM, XRD, DLS, FE-SEM, UV–Vis, EDX, XPS, TGA, NMR, VSM, ICP and elemental analysis techniques. The heterogeneous magnetic nanocatalyst can easily be recovered by an external magnetic field and reused for the next reactions for at least seven times with negligible leaching of catalyst and no substantial decrement in the activity. All these highlights have made the present protocol an interesting, simple and environmentally benign process with low catalyst loading and easy manipulations.

A new approach to large scale production of dimethyl sulfone: A promising and strong recyclable solvent for ligand-free Cu-catalyzed C-C cross-coupling reactions

Dimethyl sulfone (DMSN) was easily prepared through efficient oxidation of dimethyl sulfoxide (DMSO) and used as a strong and green solvent for organic reactions. A mixture of HNO3/NaOCl was used as an oxidizing agent for efficient oxidation of DMSO to DMSN. The effect of DMSN was evaluated for copper-catalyzed coupling reactions. It is worth noting that DMSN could play the role of a ligand for copper ions. A general survey was accomplished for various types of C-C cross-coupling reactions catalyzed by CuI in DMSN in the absence of any ligand. Moderate to good yields were achieved for Sonogashira, Heck, and Suzuki cross-coupling reactions. Finally, DMSN was recovered and reused for several consecutive runs without any loss of its activity.

Palladium nanoparticles immobilized on EDTA-modified Fe3O4@SiO2: a highly stable and efficient magnetically recoverable catalyst for the Heck–Mizoroki coupling reactions

Palladium nanoparticles supported on EDTA-modified Fe3O4@SiO2 NPs as an efficient and magnetically reusable nanocatalyst was applied for the Heck cross-coupling reactions. The catalyst was very effective for the Heck reaction of aryl halides (iodides, bromides, and chlorides) with alkenes and conversion was excellent in most cases with higher TOF (turn over frequency). Moreover, the catalyst could be recycled for eight runs without any significant loss of catalytic activity, showing its superiority over homogeneous catalysts for industrial and chemical applications. Also, the leaching of the catalyst has been examined by a hot filtration test and ICP analysis.

Bis-salophen palladium complex immobilized on Fe3O4@SiO2 nanoparticles as a highly active and durable phosphine-free catalyst for Heck and copper-free Sonogashira coupling reactions

New Fe3O4@SiO2 core-shell superparamagnetic nanoparticles functionalized by a bis-salophen Schiff base Pd complex were synthesized and employed as an efficient magnetic nanocatalyst in the Heck and Sonogashira cross coupling reactions. The synthesized nanostructures were characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), dynamic light scattering (DLS), energy dispersive X-ray analysis (EDX), X-ray photoelectron spectroscopy (XPS), elemental analysis (CHN), cyclic voltammetry (CV), Brunauer-Emmett-Teller analysis (BET), and UV-vis spectroscopy. The morphology and size of the nanoparticles were investigated by FE-SEM and TEM analyses. Furthermore, the magnetic properties of the catalyst were investigated by VSM analysis. The loading content and leaching amounts of palladium on the catalyst were measured by inductively coupled plasma (ICP) analysis. Also, the thermal behavior of this magnetic heterogeneous catalyst was studied using a TGA instrument. This heterogeneous catalytic system showed a good performance in the coupling of aryl halides with alkynes (Sonogashira reaction) as well as aryl halides with alkene derivatives (Heck reaction). High to excellent yields were achieved for these C-C coupling reactions. The catalyst can be simply separated from the reaction media by an external magnet and reused for eight consecutive runs without any significant loss of activity. Finally, the kinetics of the reactions were studied in this work.

Green, cost-effective and efficient procedure for Heck and Sonogashira coupling reactions using palladium nanoparticles supported on functionalized Fe3O4@SiO2 by polyvinyl alcohol as a highly active, durable and reusable catalyst

A novel heterogenized organometallic catalyst was synthesized by coordinating palladium with polyvinyl alcohol-functionalized Fe3O4@SiO2 nanospheres. This novel catalyst was characterized using Fourier transform infrared spectroscopy, X-ray diffraction, transmission electron microscope, field emission scanning electron microscope, dynamic light scattering, UV–vis spectroscopy, X-ray photoelectron spectroscopy, energy dispersive X-ray analysis, thermogravimetric analysis and inductively coupled plasma analysis. The prepared palladium nanoparticles supported on polyvinyl alcohol functionalized Fe3O4@SiO2 nanoparticles were successfully applied as a magnetically recyclable catalyst in Heck and Sonogashira coupling reactions in water. They showed remarkable activity toward aryl halides (I, Br, Cl) using very low palladium loading in excellent yields and demonstrated high TONs (mmol of product per mmol of catalyst). Also, the catalyst could be magnetically separated and reused seven times without any appreciable loss of catalytic activity.

A nano tetraimine Pd(0) complex: Synthesis, characterization, computational studies and catalytic applications in the Heck-Mizoroki reaction in water

A new nano tetraimine Pd(0) complex was successfully prepared by the complexation of palladium acetate with an N,N-bisimine ligand. The structural features of the catalyst and the ligand were characterized using different microscopic and spectroscopic techniques such as FT-IR, XRD, XPS, UV-Vis, NMR, and elemental analysis. The morphology of the catalyst was determined using FE-SEM and TEM. The catalyst was effectively employed in the palladium-catalyzed Heck-Mizoroki reaction in water as a green solvent. The catalyst was reusable and recycled six times without any decrease in its catalytic activity. The ICP analysis showed that the catalyst has very little Pd leaching (0.2%) during the reaction process, demonstrating that our catalyst is stable and heterogeneous in practice. Furthermore, we have theoretically explored the feasibility of two neutral and cationic pathways in the density functional theory framework. The geometries and energies of all species involved in the reaction mechanism are analyzed.

Magnetically-recoverable Schiff Base Complex of Pd (II) Immobilized on Fe3O4@SiO2 Nanoparticles: An Efficient Catalyst for Mizoroki-Heck and Suzuki-Miyaura Coupling Reactions

The activity of Pd(II)-Schiff base complexmolecules grafted on the surface of Fe3O4@SiO2 particles were investigated in the palladium-catalyzed coupling reactions of aryl halides with alkenes (Mizoroki-Heck reaction) and phenylboronic acids (Suzuki-Miyaura reaction) in the absence of phosphorous ligands. This method shows notable advantages such as heterogeneous nature of the catalyst, excellent yields, short reaction times, easy preparation, simplicity of operation, and cleaner reaction profiles. The catalyst can be separated from the reaction mixture by applying a permanent magnet externally and can be reused for several times without significant loss of activity. Also, the amount of palladium leaching has been determined by ICP analysis.

Pd-functionalized MCM-41 nanoporous silica as an efficient and reusable catalyst for promoting organic reactions

Pd-functionalized MCM-41 nanoporous silica has been explored as an efficient and recyclable catalyst to effect Suzuki and Mizoroki-Heck cross-coupling reactions, under various conditions. In Suzuki-Miyaura reactions, various aryl halides were coupled with aryl boronic acids at 100 °C under solvent-free conditions using K2CO3 as base and the maximum Ar-Ar yield reached 95%. The MCM(Pd)-41 catalyst was also used for a good range of Heck reactions using different aryl halides with styrene or n-butyl acrylate esters at 130 °C under solvent-free conditions using n-Pr3N as base that gave the maximum yields of 95% and 92%, respectively. High yield, low reaction times, non-toxicity and recyclability of the catalyst are the main merits of this protocol. The catalyst has been characterized by FT-IR, XRD, SEM, TEM, XPS, EDX, ICP-AES, TG and N2 adsorption-desorption.

Palladium catalyst supported on PEGylated imidazolium based phosphinite ionic liquid-modified magnetic silica core-shell nanoparticles: A worthy and highly water-dispersible catalyst for organic reactions in water

A highly water-dispersible palladium nanocatalyst was fabricated by the immobilization of Pd onto the surface of PEGylated imidazolium based phosphinite ionic liquid functionalized γ-Fe2O3@SiO2 core-shell nanoparticles. This nanocatalyst (denoted as [Pd@PEGylated ImIL-OPPh2-γ-Fe2O3@SiO2]) was assessed as a promising Pd catalyst in different organic reactions including Mizoroki-Heck and Sonogashira coupling reactions of aryl halides and the reduction reaction of 4-nitrophenol (4NP) to 4-aminophenol (4AP). From the application point of view, this nanocatalyst showed high thermal versatility, stability, recoverability, and compatibility in aqueous media. The catalyst recovery test revealed that its performance and catalytic activity stayed indefectible during several sequential runs. The loading level of Pd in the [Pd@PEGylated ImIL-OPPh2-γ-Fe2O3@SiO2] catalyst was 0.087 mmol g-1. Pivotal properties including high robustness, efficiency and turnover frequency (TOF), mild reaction conditions, utilization of water as a green solvent, simple product work-up, and facile catalyst recovery make this catalyst favourable from the environmental and economic points of view.