γ-Fe_2O_3:A magnetic separable catalyst for synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide

<正>An efficient route for the synthesis of 5-substituted 1H-tetrazole via[2+3]cycloaddition of nitriles and sodium azide is reported usingγ-Fe_2O_3 nanoparticles as a magnetic separable catalyst.Under optimized conditions,the moderate to good yields(71-95%) can be obtained.The catalyst can be easily separated by a magnet and reused for several circles.     

Cu(II)–Schiff base complex‐functionalized magnetic Fe3O4 nanoparticles: a heterogeneous catalyst for various oxidation reactions

Cu(II)–Schiff base complex‐functionalized magnetic Fe₃O₄ nanoparticles were prepared and characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis and scanning electron microscopy techniques. This compound acts as a highly active and selective catalyst for the oxidation of sulfides and thiols. These reactions can be carried out in ethanol or solvent‐free conditions in the presence of hydrogen peroxide with complete selectivity and very high conversion under mild reaction conditions. The designed catalytic system prevents effectively the over‐oxidation of sulfides to sulfones. Separation and recycling can also be easily done using a simple magnetic separation process. Copyright © 2015 John Wiley & Sons, Ltd.     

Immobilization of palladium nanoparticles on ionic liquid-triethylammonium chloride functionalized magnetic nanoparticles: As a magnetically separable,stable and recyclable catalyst for Suzuki-Miyaura cross-coupling reactions

A facile procedure was applied to successfully synthesize novel Pd nanoparticles immobilized on triethanolamine-functionalized magnetic nanoparticles [Fe₃O₄/IL/Pd]. Diverse characterizations (HR-TEM, XRD, FT-IR, TGA, EDX, FE-SEM, ICP, XPS and VSM) were carried out to identify intrinsic traits of the nanoparticles. At room temperature, Fe₃O₄/IL/Pd demonstrated high catalytic activity toward Suzuki-Miyaura cross-coupling reactions in aqueous solution. Based on the results, Fe₃O₄/IL/Pd acted as zwitterionic IL-type heterogeneous catalyst, which could be separated from the reaction mixture, conveniently. Moreover, it exhibited excellent recyclability for at least eight cycles without considerable loss of its activity.     

可重复使用CuO纳米粒子催化微波辅助的腈和NaN3环加成反应 合成5-取代1H-四唑类

将可重复使用的CuO纳米粒子成功用于催化微波辅助的腈和NaN3[3+2]环加成反应高效合成5-取代1H-四唑类化合物.该法突出特点为成本低、合成快、稳定性高、可重复使用、反应条件温和、无需任何添加物、官能团兼容性好和产率高.这种环境友好的微波辅助纳米粒子催化合成策略可望替代现有的涉及常规路易斯酸催化剂方法,以及作为一种简易的合成特殊化合物的方法.     

Diisopropylethylammonium acetate (DIPEAc): An efficient and recyclable catalyst for the rapid synthesis of 5-substituted-1H-tetrazoles

A simple and efficient protocol developed for the synthesis of 5-substituted 1H-tetrazole derivatives through [2+3] cycloaddition reaction between benzonitriles and sodium azide using diisopropylethylammonium acetate as a recyclable reaction medium is described. The reactions proceed well at 80?°C and provide the corresponding tetrazoles in good to excellent yields (up to 94% yield). Developed method has notable advantages, such as simple and mild conditions, easy workup, reusability with consistent catalytic activity, and safer alternative to hazardous, corrosive conventional Lewis acid catalysts.     

Synthesis of 5-substituted 1H-tetrazoles and oxidation of sulfides by using boehmite nanoparticles/nickel-curcumin as a robust and extremely efficient green nanocatalyst

Nickel-anchored curcumin-functionalized boehmite nanoparticles (BNPs@Cur-Ni) as a robust and versatile nanocatalyst was synthesized and well-characterized by using Fourier transform infrared (FT-IR), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray (EDX), X-ray mapping, thermogravimetric analysis (TGA), differential thermal analysis (DTA), Brunauer–Emmett–Teller (BET), X-ray diffraction (XRD), and inductively coupled plasma optical emission spectroscopy (ICP-OES). The synthesis of 5-substituted 1H-tetrazoles and the oxidation of sulfides were conducted by BNPs@Cur-Ni with excellent turnover number (TON) and turnover frequency (TOF) outcomes. Also, the catalyst was reused for several sequential runs without Ni leaching or decreasing in reaction yield. Utilizing the curcumin and boehmite with a natural source as well as poly(ethylene glycol) (PEG) as a solvent in this simple protocol can be based on green chemistry rules.     

Synthesis and characterization of sulfamic acid supported on Fe3O4 nanoparticles: A green,versatile and magnetically separable acidic catalyst for oxidation reactions and Knoevenagel condensation

Sulfamic acid immobilized on diethylenetriamine functionalized Fe₃O₄ nanoparticles (SA‐DETA‐Fe₃O₄) was successfully prepared and characterized by X‐ray diffraction (XRD), Fourier transform infrared spectroscopy (FT‐IR), vibrating sample magnetometer (VSM), thermo gravimetric analysis (TGA), X‐Ray diffraction (XRD) and scanning electron microscopy (SEM). The sulfamic acid was found as a magnetically separable and highly active catalyst for the oxidative coupling thiols, oxidation of sulfides. Furthermore, the SA‐DETA‐Fe₃O₄ showed the high catalytic activity in Knoevenagel condensation of aromatic aldehydes with active methylene compounds (malononitrile and ethyl cynoacetate). The nanosolid catalyst could be easily recovered by a simple magnetic separation and reused for many cycles without deterioration in catalytic activity.     

Simple synthesis of Pd-Fe3O4 heterodimer nanocrystals and their application as a magnetically recyclable catalyst for Suzuki cross-coupling reactions

A simple gram-scale synthesis of Pd-Fe(3)O(4) heterodimer nanocrystals was achieved by controlled one-pot thermolysis of a mixture solution composed of iron acetylacetonate, palladium acetylacetonate, oleylamine, and oleic acid. The heterodimer nanocrystals are composed of a 6 nm-sized Pd nanosphere and a 30 nm-sized faceted Fe(3)O(4) nanocrystal and they are soft ferrimagnetic with high saturation magnetization value and low coercivity value. The heterodimer nanocrystals exhibited good activities for various Suzuki coupling reactions. Furthermore, the nanocrystal catalyst could be easily separated from the product mixture by using a magnet and could be recycled 10 times without losing catalytic activity.     

Silica-coated magnetic nanoparticles functionalized cobalt complex: a recyclable and efficient catalyst for the C−C bond formation

In this study, the Co-based catalyst was prepared by cobalt immobilization on the surface of functionalized silica-coated magnetic NPs (Fe₃O₄@SiO₂-CT-Co) as a magnetically core–shell nanocatalyst and characterized by FT-IR, TGA, XRD, VSM, SEM, TEM, EDX, EDX mapping, and ICP techniques and appraised in the Suzuki–Miyaura cross-coupling reaction under mild reaction conditions. The results displayed the superparamagnetic behavior of the Fe₃O₄ NPs core encapsulated by SiO₂ shell, and the size of the particles was estimated about 30 nm. Compared with the previously reported catalysts, the engineered Fe₃O₄@SiO₂-CT-Co catalyst provided perfect catalytic performance for the Suzuki–Miyaura cross-coupling reaction in water as a green solvent and it was much cheaper in the comparison with the traditional Pd-based catalysts. Importantly, the durability of magnetic nanocatalyst was studied and observed that it is stable under the reaction conditions and could be easily reused for at least six successive cycles without any significant decrease in its catalytic activity.

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Facile synthesis of hierarchical core-shell Fe3O4@MgAl-LDH@Au as magnetically recyclable catalysts for catalytic oxidation of alcohols

A novel core-shell structural Fe(3)O(4)@MgAl-LDH@Au nanocatalyst was simply synthesized via supporting Au nanoparticles on the MgAl-LDH surface of Fe(3)O(4)@MgAl-LDH nanospheres. The catalyst exhibited excellent activity for the oxidation of 1-phenylethanol, and can be effectively recovered by using an external magnetic field.     

Immobilized palladium on surface-modified Fe3O4/SiO2 nanoparticles: as a magnetically separable and stable recyclable high-performance catalyst for Suzuki and Heck cross-coupling reactions

A palladium-based catalyst (Fe₃O₄/SiO₂/HPG–OPPh₂–PNP) supported on chlorodiphenylphosphine-functionalized magnetic nanoparticles was successfully prepared from Fe₃O₄/SiO₂ with sequential attachment of glycerol and chlorodiphenylphosphine, followed by treatment of an ethanolic solution of palladium chloride with hydrazine. The as-prepared catalyst was characterized by ICP-AES, FTIR, XRD, SEM, and TEM. The Fe₃O₄/SiO₂/HPG–OPPh₂–PNP was found as a magnetically separable and highly active catalyst for Suzuki coupling reactions of aryl iodides, bromides, and chlorides as well as Heck reactions of aryl iodides and bromides. Under appropriate conditions, all reactions afforded the desired products in moderate to excellent yields. Moreover, this catalyst can be easily recovered by using a magnetic field and directly reused for at least six cycles without significant loss of its activity.     

Copper Schiff base complex immobilized on silica‐coated Fe3O4 nanoparticles: a recoverable and efficient catalyst for synthesis of polysubstituted pyrroles

In this work, a copper Schiff base complex immobilized on silica‐coated Fe₃O₄ nanoparticles is synthesized, and studied as a highly efficient, recyclable, green and heterogeneous catalyst for the preparation of polysubstituted pyrroles under solvent‐free and mild conditions. This new catalyst was characterized by different techniques, such as Fourier transform infrared (FT‐IR), X‐ray powder diffraction (XRD), field‐emission scanning electron microscopy (SEM), energy‐dispersive X‐ray spectroscopy (EDX), inductively coupled plasma (ICP) and vibrating sample magnetometry (VSM). The simple and environmentally one‐pot multicomponent condensation of nitromethane, an aryl aldehyde, a 1,3‐dicarbonyl compound and an amine in the presence of above catalyst affords the title compounds at room temperature. At the end, we compared the results for the synthesis of polysubstituted pyrroles in the presence of our nanocatalyst with previously reported catalysts in the literature.     

Dendrimer‐encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe3O4@SiO2 nanoparticles as a novel recyclable catalyst for N‐arylation of nitrogen heterocycles and green synthesis of 5‐substituted 1H‐tetrazoles

In this study, dendrimer‐encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe₃O₄@SiO₂ nanoparticles were prepared via a multistep‐synthesis. Then, the synthesized composite was fully characterized by various techniques such as fourier transform infrared (FT‐IR) spectroscopy, X‐ray diffraction (XRD), dynamic light scattering (DLS), UV‐vis spectroscopy, energy dispersive X‐ray analysis (EDX), thermogravimetric analysis (TGA) and vibration sample magnetometer (VSM). From the information gained by FE‐SEM and TEM studies it can be inferred that the particles are mostly spherical in shape and have an average size of 50 nm. Also, the amount of Cu is determined to be 0.51 mmol/g in the catalyst by inductively coupled plasma (ICP) analyzer. This magnetic nano‐compound has been successfully applied as a highly efficient, magnetically recoverable and stable catalyst for N‐arylation of nitrogen heterocycles with aryl halides (I, Br) and arylboronic acids without using external ligands or additives. The catalyst was also employed in a one‐pot, three‐component reaction for the efficient and green synthesis of 5‐substituted 1H‐tetrazoles using various aldehydes, hydroxylamine hydrochloride and sodium azide in water. The magnetic catalyst can be easily separated by an external magnet bar and is recycled seven times without significant loss of its activity.     

One-pot synthesis of Ag-Fe3O4 nanocomposite: a magnetically recyclable and efficient catalyst for epoxidation of styrene

With the assistance of PVP, a novel magnetically recyclable Ag-based catalyst has been synthesized in one pot, and it is found that this catalyst is highly efficient in selectively catalyzing styrene conversion to styrene oxide.     

Immobilized manganese porphyrin on functionalized magnetic nanoparticles via axial ligation: efficient and recyclable nanocatalyst for oxidation reactions

Magnetic nanoparticles (MNPs), Fe₃O₄@SiO₂, have been prepared and functionalized by 3-(chloropropyl)trimethoxysilane and then by imidazole to synthesize Fe₃O₄@SiO₂-Im. The functionalized Fe₃O₄ nanoparticles were used as a support to anchor manganese porphyrin via axial ligation. The prepared catalyst was characterized by elemental analysis, FT-IR spectroscopy, X-ray powder diffraction, UV–vis spectroscopy, and scanning electron microscopy. Application of immobilized manganese porphyrin as a heterogeneous catalyst in oxidation of alkenes and sulfides was explored. To find suitable reaction conditions, effect of different parameters such as solvent and temperature on immobilization process and also various reaction parameters (oxidant, solvent, and time) on oxidation reactions has been investigated. The results showed that the immobilized Mn-porphyrin on functionalized MNPs is an efficient and reusable catalyst for oxidation of substrates.     

A robust and recyclable ionic liquid-supported copper(II) catalyst for the synthesis of 5-substituted-1H-tetrazoles using microwave irradiation

Research on Chemical Intermediates - A novel and robust ionic liquid-supported copper(II) catalyst has been developed and explored for the efficient synthesis of 5-substituted-1H-tetrazoles using...