A novel chiral manganese-tetraamide macrocycle complex covalently attached to magnetite as recyclable catalyst for aerobic asymmetric epoxidation of olefins

Hadian-Dehkordi, Leila; Hosseini‐Monfared, Hassan; Aleshkevych, P.

doi:10.1016/j.ica.2017.03.019

Cited by 15 publications

(7 citation statements)

References 57 publications

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“…The catalytic sufficiency of Cu‐PST was remarkably motivated by the nature of the applied solvent in the 1,2‐cyclooctene and benzyl alcohol (ep)oxidation, which were studied recently with different oxidants . The effects of alternative solvents, i.e.…”

Section: Resultsmentioning

confidence: 99%

“…The emphasis was on organocatalysts immobilization on Fe 3 O 4 coated with SiO 2 and the need for functional active reagents, for example CPTMS (3‐chloroopropyltrimethoxysilane) or APTES (3‐aminopropyltriethoxysilane) . To save their cost and to reduce the synthetic steps for preparation of supported organocatalysts on Fe 3 O 4 ‐SiO 2 , significant functional groups in the backbone of the coordinated ligands to the central metal ion of the catalyst could interact with Fe 3 O 4 ‐SiO 2 nanoparticles to be immobilized on it, for example ―OH and ―OR groups …”

Section: Introductionmentioning

confidence: 99%

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Catalytic evaluation of copper (II)N‐salicylidene‐amino acid Schiff base in the various catalytic processes

Al-Hussein

Adam

2020

Applied Organom Chemis

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N‐Salicylidene amino acid Schiff base sodium sulfonate salt, as a tridentate dibasic chelating ligand, was obtained from the common condensation of salicylaldehyde‐5‐sodium sulfonate with tyrosine (HPST). The internal formed ligand coordinated to Cu2+ ion in an aqueous media affording new Cu (II)‐complex (Cu‐PST), which characterized by various physico‐chemicals spectral tools. The mononuclear complex was evaluated as a homogeneous and heterogeneous catalyst in the (ep)oxidation protocols of 1,2‐cyclooctene and benzyl alcohol. Heterogeneously, Cu‐PST was immobilized on Fe3O4‐SiO2, as nanoparticles. The heterogeneous catalyst was characterized by infrared, X‐ray diffraction, scanning electron microscopy, transmission electron microscopy, energy‐dispersive spectroscopy, Brunauer−Emmett−Teller and magnetism. Homogeneously, the temperature, solvent and oxidant influences were examined in the catalytic reactions to realize the best reaction conditions. Cu‐catalyst exhibited better catalytic performance in the (ep)oxidation processes homogeneously than that in the heterogeneous phase at 80°C for 2 hr in acetonitrile. Reusability of the homogeneous catalyst was for a maximum of three times in the (ep)oxidation reaction, whereas the heterogeneous catalyst was active for six times. A mechanistic pathway was proposed for both catalysts, comparatively.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Catalytic evaluation of copper (II)N‐salicylidene‐amino acid Schiff base in the various catalytic processes

Al-Hussein

Adam

2020

Applied Organom Chemis

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“…Through many types of support, immobilization of transition metal complexes to the surface of nanosheets, nanotubes, and nanomaterials, especially magnetic nanoparticles, attracted more attention. The magnetic nanoparticles like Fe 3 O 4 , due to their advantages such as low cost, chemical and high thermal stability, non-toxic, strong magnetization, and easy separation would be the most bene cial candidate for functionalization of complexes [27][28][29]. Herein, in accordance with green chemistry importance and application of epoxies, Mn-porphyrin immobilized onto the surface of magnetic nanoparticles (MNPs) with different linker lengths and used for oxidation of different ole ns with molecular oxygen.…”

Section: Introductionmentioning

confidence: 99%

Mn-porphyrins Anchored onto Magnetic Nanoparticles via Different Linker Length: A Comparative Study in Aerobic Oxidation of Olefins

Rayati¹,

Shokoohi²

2022

Preprint

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In this research, meso-tetrakis(4-carboxyphenyl)porphyrinatomanganese(III) acetate has been immobilized onto the modified silica-coated Fe3O4 nanoparticles with linkers with different chain lengths (short, Fe3O4@SiO2-MnTCPP (C-1), medium Fe3O4@SiO2-NH2-MnTCPP (C-2), and long length, Fe3O4@SiO2-NHCO-NH2-MnTCPP (C-3)). The catalysts were characterized by various analytical and spectroscopic methods, including FT-IR, UV-Vis, XRD, FE-SEM, TEM, TGA, and VSM. A comparative study based on the difference in chain length of the linker in the oxidation of olefins with molecular oxygen was performed. The novel linker (long-chain catalyst) was designed to improve the performance of the catalytic activity (complete conversion of the α-methyl styrene, 4-methyl styrene and 4-chloro styrene was achieved after 2 h). The new heterogenized catalyst (Fe3O4@SiO2-NHCO-NH2-MnTCPP) not only shows higher catalytic activity in the oxidation of different olefins, but also shows better reusability of the catalyst.

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“…[ 21,22 ] Recently, research studies focused on the synthesis of new and highly magnetic transition metal oxides covered by a shell of SiO 2 and supported an inorganic‐organocatalyst to be used as a heterogeneous catalyst. [ 23–26 ]…”

Section: Introductionmentioning

confidence: 99%

“…Interestingly, the immobilization of the hybrid inorganic‐organocatalysts on the Fe 3 O 4 surface and on the Fe 3 O 4 surface coated with SiO 2 requires ultimate active functional chains, preferably, 3‐haloalkyltrialkoxysilane [ 23 ] and 3‐aminoalkyltrialkoxysilicate (i.e., cross‐linking bonds). [ 24–26 ] The high cost and additional synthetic routes of the immobilization of inorganic‐organocatalysts cause more complications. [ 16,17,20 ] Such promoted immobilization could be accomplished easily with specific functional groups in the coordinated ligand backbone of the inorganic‐organocatalysts, for example, alkoxy (–OR) [ 27 ] or hydroxyl (–OH) groups.…”

Section: Introductionmentioning

confidence: 99%

Nanocomposite‐based inorganic‐organocatalyst Cu(II) complex and SiO₂‐ and Fe₃O₄ nanoparticles as low‐cost and efficient catalysts for aniline and 2‐aminopyridine oxidation

Adam

Al‐Omair

2020

Applied Organom Chemis

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Bis‐imino Cu(II) complex (CuLAn2), in which the imine ligand (HLAn) acts as a bidentate chelating ligand, was synthesized. The catalytic potential of the inorganic‐organocatalyst was studied homogeneously and heterogeneously in the oxidation of aniline and 2‐aminopyridine by H2O2 or tBuOOH. Two heterogeneous inorganic‐organocatalysts, CuLAn2@Fe3O4 and CuLAn2@SiO2@Fe3O4, were synthesized by the successful immobilization of CuLAn2 on the Fe3O4 surface and the composited Fe3O4 with SiO2, respectively. The heterogeneous structure of those inorganic‐organocatalysts was confirmed using Fourier‐transform infrared, scanning electron microscopy, energy‐dispersive X‐ray spectroscopy, X‐ray diffraction, transmission electron microscopy, and magnetic properties. The adsorption–desorption isotherms revealed respectable adsorption parameters (SBET, Vp, and rp). All catalysts exhibited high potential in the oxidation of aniline (with phenylhydroxylamine as the main product) and good potential in the oxidation of 2‐aminopyridine, in the first attempt (with 2‐nitropyridine‐N‐oxide and 2‐nitrosopyridine‐N‐oxide as main products), at room temperature. Acetonitrile was found to be the best solvent compared to ethanol, dimethyl sulfoxide, chloroform, and water. The homogeneous catalyst exhibited reusability for three times. The heterogeneous catalysts, CuLAn2@Fe3O4 and CuLAn2@SiO2@Fe3O4, were active for five and seven times, respectively. A mechanism was proposed within electron and oxygen transfer processes.

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A novel chiral manganese-tetraamide macrocycle complex covalently attached to magnetite as recyclable catalyst for aerobic asymmetric epoxidation of olefins

Cited by 15 publications

References 57 publications

Catalytic evaluation of copper (II)N‐salicylidene‐amino acid Schiff base in the various catalytic processes

Catalytic evaluation of copper (II)N‐salicylidene‐amino acid Schiff base in the various catalytic processes

Mn-porphyrins Anchored onto Magnetic Nanoparticles via Different Linker Length: A Comparative Study in Aerobic Oxidation of Olefins

Nanocomposite‐based inorganic‐organocatalyst Cu(II) complex and SiO₂‐ and Fe₃O₄ nanoparticles as low‐cost and efficient catalysts for aniline and 2‐aminopyridine oxidation

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A novel chiral manganese-tetraamide macrocycle complex covalently attached to magnetite as recyclable catalyst for aerobic asymmetric epoxidation of olefins

Cited by 15 publications

References 57 publications

Catalytic evaluation of copper (II)N‐salicylidene‐amino acid Schiff base in the various catalytic processes

Catalytic evaluation of copper (II)N‐salicylidene‐amino acid Schiff base in the various catalytic processes

Mn-porphyrins Anchored onto Magnetic Nanoparticles via Different Linker Length: A Comparative Study in Aerobic Oxidation of Olefins

Nanocomposite‐based inorganic‐organocatalyst Cu(II) complex and SiO2‐ and Fe3O4 nanoparticles as low‐cost and efficient catalysts for aniline and 2‐aminopyridine oxidation

Contact Info

Product

Resources

About

Nanocomposite‐based inorganic‐organocatalyst Cu(II) complex and SiO₂‐ and Fe₃O₄ nanoparticles as low‐cost and efficient catalysts for aniline and 2‐aminopyridine oxidation