Synthesis, characterization, and immobilization of nickel(II) tetradentate Schiff-base complexes on clay as heterogeneous catalysts for the oxidation of cyclooctene

Bezaatpour, Abolfazl; Amiri, Mandana; Jahed, Vahdat

doi:10.1080/00958972.2011.582582

Cited by 32 publications

(9 citation statements)

References 33 publications

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“…According to this study and also by comparison with the literature, a mechanism for oxidation of various sulfides to sulfoxides using [WO(O 2 )L(CH 3 OH)] was proposed (scheme 2). The reaction proceeds with nucleophilic attack of the uncoordinated sulfide on one oxygen of the peroxido, The epoxidation of olefins to epoxides is a valuable transformation for organic synthesis since epoxides are highly important intermediates in the preparation of various chemically and biologically active compounds [17][18][19]. High-valent metal oxido-peroxido species have demonstrated the ability to catalyze the epoxidation of alkenes, via homogeneous as well as heterogeneous routes [10,20].…”

Section: Catalytic Reactivitymentioning

confidence: 99%

Catalytic efficacy of an oxido-peroxido tungsten(VI) complex: synthesis, X-ray structure and oxidation of sulfides and olefins

Amini

Bagherzadeh

Eftekhari‐Sis

et al. 2013

Journal of Coordination Chemistry

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An oxido-peroxido tungsten(VI) complex [WO(O 2 )L(CH 3 OH)] using salicylidene benzoyl hydrazine as a tridentate ONO donor Schiff base (H 2 L) has been synthesized and characterized by elemental analysis, IR, 1 H NMR, molar conductance data, and single-crystal X-ray analysis. The complex was used as a catalyst for epoxidation of olefins and oxidation of sulfides. The results show that epoxides and sulfoxides were produced in high yield, turnover number, and selectivity. IntroductionOxido and peroxido transition metal compounds have played an important role in oxidation of organic substrates. A variety of peroxido complexes of various metals are known to catalyze the oxidation of olefins, arenes, phenols, alcohols, phosphines, and sulfides [1-3]. The catalytic activity of peroxido metal complexes is influenced by the type of metal, the number of peroxido ligands attached to the catalyst and the nature of the remaining ligands in the coordination sphere [3][4][5][6].Current interest in tungsten is due to the importance of the metal as an essential trace element that participates in a number of important enzymatic reactions [7]. There are a few reports on preparation and catalytic activity of oxido-peroxide tungsten(VI) complexes in oxidation reactions [8][9][10].We recently reported a highly efficient method for oxidation of olefins and sulfides by using an oxido-peroxido Mo(VI) complex [MoO(O 2 )L(CH 3 OH)] with salicylidene benzoyl hydrazine (H 2 L) as ligand [11]. In order to study the effect of metal on catalytic reactivity, herein we report the synthesis, characterization, and comparative catalytic activity of a new oxido-peroxido W(VI) complex [WO(O 2 )L(CH 3 OH)] in oxidation of olefins and sulfides under the same condition as given in our previous work (scheme 1).

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Section: Catalytic Reactivitymentioning

confidence: 99%

Catalytic efficacy of an oxido-peroxido tungsten(VI) complex: synthesis, X-ray structure and oxidation of sulfides and olefins

Amini

Bagherzadeh

Eftekhari‐Sis

et al. 2013

Journal of Coordination Chemistry

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“…[16,[26][27][28][29][30] Magnetic separation renders the recycling of catalysts from solution using external magnetic fields much easier than filtration and centrifugation. In continuation of our previous investigation of catalytic activity of Schiff base complexes, [6,[9][10][11]15,19] herein we report the anchoring of novel cisdioxomolybdenum(VI) macrocyclic Schiff base complex by reaction of 1,4-bis(2-carboxyaldehydephenoxy)butane, MoO 2 Cl 2 (DMF) 2 and amino-modified magnetite nanoparticles (Scheme 1). The new nanocatalyst (Fe 3 O 4 @SiO 2 -(CH 2 ) 3 -PBSB/MoO 2 ) was characterized using Fourier transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), diffuse reflectance spectroscopy (DRS), vibrating sample magnetometry (VSM), energy-dispersive X-ray spectroscopy (EDX) and powder X-ray diffraction (XRD), and tested for epoxidation of internal alkenes (cyclohexene, cyclooctene, α-pinene, indene, trans-stilbene) and terminal alkenes (1-heptene, 1-octene, 1-dodecene, styrene) with TBHP (80% in di-tert-butyl peroxide-water, 3:2) as oxidant.…”

Section: Introductionmentioning

confidence: 99%

“…[14] Therefore, supporting of metal complexes has been the subject of a lot of research in catalytic fields. [15][16][17][18] A main idea for supporting of metal complexes is to anchor the metal complexes onto large-surface-area inorganic materials such as zeolites and metal oxides. [16,[19][20][21][22][23][24][25] Nowadays, magnetite nanoparticles are of particular interest because of their unique properties including high surface area, low toxicity, ability to be separated and biocompatibility.…”

Section: Introductionmentioning

confidence: 99%

Excellent alkene epoxidation catalytic activity of macrocyclic‐based complex of dioxo‐Mo(VI) on supermagnetic separable nanocatalyst

Payami

Bezaatpour

Eskandari

2017

Applied Organom Chemis

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A phenoxybutane-based Schiff base complex of cis-dioxo-Mo(VI) was supported on paramagnetic nanoparticles and characterized using powder Xray diffraction, infrared, diffuse reflectance and atomic absorption spectroscopies, scanning and transmission electron microscopies and vibrating sample magnetometry. The separable nanocatalyst was tested for the selective epoxidation of cyclohexene, cyclooctene, styrene, indene, α-pinene, 1-octene, 1-heptene, 1-dodecene and trans-stilbene using tert-butyl hydroperoxide (80% in di-tert-butyl peroxide-water, 3:2) as oxidant in chloroform. The catalyst was efficient for oxidation of cyclooctene with 100% selectivity for epoxidation with 98% conversion in 10 min. We were able to separate magnetically the nanocatalyst using an external magnetic field and used the catalyst at least six successive times without significant decrease in conversion.The turnover frequency of the catalyst was remarkable (2556 h −1 for cyclooctene). The proposed nanomagnetic catalyst has advantages in terms of catalytic activity, selectivity, catalytic reaction time and reusability by easy separation.

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“…According to our previous works on the catalytic activity of d‐block Schiff base complexes, a MnFe] 2 O 4 supported Mo(VI) Schiff base complex, MnFe 2 O 4 ‐Mo(VI), derived from 1,3‐bis(4‐bromo‐2‐carboxyaldehyde phenoxy)propane has been developed in the presented work (Figure ). The novel heterogeneous catalyst was tested for its ability to oxidize olefins and sulfides selectively into epoxides and sulfoxides in green solvent‐less condition.…”

Section: Introductionmentioning

confidence: 77%

Manganese Ferrite Nanoparticles Modified by Mo(VI) Complex: Highly Efficient Catalyst for Sulfides and Olefins Oxidation Under Solvent‐less Condition

et al. 2019

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In this research work, we report a new Mo(VI) Schiff base complex based on 1,3‐bis(4‐bromo‐2‐carboxyaldehyde phenoxy)propane, which was immobilized covalently on MnFe2O4 magnetic nanoparticles. The efficiency of the novel catalyst was investigated for the oxidation of olefins and organic sulfides. Under optimized conditions, the nanoparticle catalyst allowed selective epoxidation of cis‐cyclooctene, cyclohexene, and cis‐cyclodecane with 99% conversion in 10 min under solvent‐free condition with tert‐butyl hydroperoxide as oxidant. The catalyst also showed excellent ability for the oxidation of thioanisole, dimethyl sulfide and benzyl phenyl sulfide with a 99% conversion in 5 min and solvent‐less condition with H2O2 (30%) as oxidant. The recyclability of catalyst was also investigated in the oxidation of cyclooctene and methyl phenyl sulfide at least for 5 times.

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Synthesis, characterization, and immobilization of nickel(II) tetradentate Schiff-base complexes on clay as heterogeneous catalysts for the oxidation of cyclooctene

Cited by 32 publications

References 33 publications

Catalytic efficacy of an oxido-peroxido tungsten(VI) complex: synthesis, X-ray structure and oxidation of sulfides and olefins

Catalytic efficacy of an oxido-peroxido tungsten(VI) complex: synthesis, X-ray structure and oxidation of sulfides and olefins

Excellent alkene epoxidation catalytic activity of macrocyclic‐based complex of dioxo‐Mo(VI) on supermagnetic separable nanocatalyst

Manganese Ferrite Nanoparticles Modified by Mo(VI) Complex: Highly Efficient Catalyst for Sulfides and Olefins Oxidation Under Solvent‐less Condition

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