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cis-Dioxo-molybdenum(VI)-oxazoline complex catalyzed epoxidation of olefins by tert-butyl hydrogen peroxide
, Article Inorganica Chimica Acta ; Volume 362, Issue 10 , 2009 , Pages 3698-3702 ; 00201693 (ISSN) ; Tahsini, L ; Latifi, R ; Keith Woo, L ; Sharif University of Technology
2009
Abstract
A new efficient catalytic system was investigated for the epoxidation of various olefins by cis-dioxo-bis[2-(2′-hydroxyphenyl)-oxazolinato]molybdenum(VI), cis-[MoO2(phox)2], and TBHP as oxidizing agent. Using this system as catalyst for the oxidation of aliphatic substrates at 80 °C gives the epoxide as the sole product with yields up to 100% and turnover frequency up to 5000 h-1. The efficiency of the catalyst is strongly influenced by the nature of solvent, reaction time and temperature, and a significant increase in the epoxide yields is observed in higher temperatures and longer reaction times. © 2009 Elsevier B.V
A new and highly effective method for catalytic oxidation of alcohols to the corresponding carbonyl compounds using the tris[(2-oxazolinyl)phenolato] manganese(III)/Oxone®/n-Bu4NBr oxidation system
, Article Tetrahedron Letters ; Volume 44, Issue 50 , 2003 , Pages 8943-8945 ; 00404039 (ISSN) ; Sharif University of Technology
Elsevier Ltd
2003
Abstract
Oxone® (2KHSO5·KHSO4·K 2SO4) in the presence of mer-tris[(2-oxazolinyl)phenolato] manganese(III), Mn(phox)3, as catalyst under biphasic reaction conditions (CH2Cl2/H2O) and tetra-n-butylammonium bromide as phase transfer agent efficiently oxidises alcohols to their corresponding aldehydes and ketones at room temperature with very short reaction times (5 min) and good to quantitative yields. © 2003 Elsevier Ltd. All rights reserved
Tris[(2-oxazolinyl)phenolato]manganese(III) as catalyst for mild and efficient oxidation of sulfides to sulfones with Oxone®
, Article Journal of Chemical Research - Part S ; Issue 12 , 2003 , Pages 765-767 ; 03082342 (ISSN) ; Sharif University of Technology
Scientific Reviews Ltd
2003
Abstract
Tris[(2-oxazolinyl)phenolato]manganese(III), Mn(phox)3, catalysed oxidation of dialkyl, diaryl, dibenzyl, and alkyl aryl sulfides to the corresponding sulfones is carried out by Oxone® in biphasic conditions (CH2Cl2/H2O), in the presence of tetra n-butylammonium bromide as phase transfer agent at room temperature in very short reaction times (5 min.) with quantitative yields
Synthesis and Characterization of a novel Ruthenium(II) Complex With Bidentate O,N-donor OxazolineLigand and Study of Catalytic Oxidation of Sulfides and Alkanes
, M.Sc. Thesis Sharif University of Technology ; Bagherzadeh, Mojtaba (Supervisor)
Abstract
The 2-(2′-hydroxyphenyl)-oxazoline ligand (Hphox) is generated from 1:1 condensation of methyl salicylate with 2-aminoethanol. Novel [Ru(Hphox)2(H2O)2] (Hphox = 2-(2′-hydroxyphenyl)-oxazoline ) complex has been synthesized and characterized by physic-chemical methods. Oxidation of sulfides catalyzed by the mixed-ligand ruthenium(II) complex [Ru(Hphox)2(H2O)2]using urea-hydrogen peroxide (UHP) as oxidant was investigated under mild condition within 1 h. The results showed that mixed-ligand ruthenium(II) complex was effective catalyst in oxidation of sulfides in whichsulfoxideswere the only products. Using this catalytic system in the oxidation of alkanes, ketones were obtained as the main...
Synthesis of some Cu(II) - 2-(2'-hydroxyphenyl)-2-oxazoline and Mn(III) - 2-(2',4'-dihydroxyphenyl)-2-oxazoline Complexes and their Application as Catalysts in Sulfides and Alcohols Oxidations
, M.Sc. Thesis Sharif University of Technology ; Bagherzadeh, Mojtaba (Supervisor)
Abstract
In this project two manganese(III) complexes with 2-(2',4'-dihydroxyphenyl)-2-oxazoline ligand, [Mn(4-OHphox)3], [Mn(4-OHphox)2(CH3OH)2]ClO4 and a copper(II) complex with 2-(2'-hydroxy)-2-oxazoline ligand have been synthesized. The complexes and the ligands were characterized by elemental analysis (CHN), FT-IR and 1HNMR spectroscopies. Oxidation of sulfides catalyzed by these complexes using urea-hydrogen peroxide (UHP) as oxidant within short reaction times (5 min) was investigated. The results showed that catalytic efficiency of [Mn(4-OHphox)3] complex was better than other complexes. Optimization of the catalyst system presented a high selectivity of sulfoxide (90-100%) in a few time (5...
Catalytic activity of manganese(III)-oxazoline complexes in urea hydrogen peroxide epoxidation of olefins: The effect of axial ligands
, Article Journal of Molecular Catalysis A: Chemical ; Volume 260, Issue 1-2 , 2006 , Pages 163-169 ; 13811169 (ISSN) ; Latifi, R ; Tahsini, L ; Sharif University of Technology
2006
Abstract
The catalytic activity of two manganese(III)-oxazoline complexes [Mn(phox)2(CH3OH)2]ClO4 and Mn(phox)3 (Hphox = 2-(2′-hydroxylphenyl)oxazoline), was studied in the epoxidation of various olefins. All of epoxidation reactions were carried out in (1:1) mixture of methanol:dichloromethane at room temperature using urea hydrogen peroxide (UHP) as oxidant and imidazole as co-catalyst. The epoxide yields clearly demonstrate the influence of steric and electronic properties of olefins, the catalysts and nitrogenous bases as axial ligand. [Mn(phox)2(CH3OH)2]ClO4 catalyst with low steric properties has higher catalytic activity than Mn(phox)3. The highest epoxide yield (95%) was achieved for indene...
Synthesis and Study of Catalytic Activity of Iron (III)-bis(2-oxazolinyl) Methane complex by Urea Hydrogen Peroxide in Oxidation of Sulfides
, M.Sc. Thesis Sharif University of Technology ; Bagherzadeh, Mojtaba (Supervisor)
Abstract
Considerable effort has been directed in recent years towards the transition metal complex catalyzed oxidation of organic compounds. Herein the synthsis of the iron complex of bis(oxazoline) ligand as a novel catalyst is reported, and the catalytic activity of this complex in oxidation of sulfides is investigated. Bis(2-oxazolynil)methane as ligand is prepared by condensation of diethylmalonate with 2-aminoethanole in 1:2 molar ratio and finally corresponding complex is synthesized by the reaction between FeCl3.6H2O and Bis(2-Oxazolynil)methane in 1:1 molar ratio. The complex is characterized by using IR, UV-Vis, cyclic voltametery, conductometery and elemental analysis data. Moreover,...
Synthesis and Characterization of Bis[2-(2׳-Hydroxyphenyl)- -oxazolinato]Ni(II) Complex and Investigation of it׳s Catalytic Activity in C-C Coupling Heck Reaction
, M.Sc. Thesis Sharif University of Technology ; Bagherzadeh, Mojtaba (Supervisor)
Abstract
In this study a new Ni(II)-¬oxazoline complex was synthesized by reaction of Ni(CH3COO)2.4H2O and 2-(2׳-hydroxyphenyl)-2-oxazoline ligand in MeOH solvent. The resulting complex bis[2-(2׳-hydroxyphenyl)-2-oxazolinato]Ni(II), was characterized by different spectroscopic methods. X-ray diffraction showed that this complex is four coordinated with a square planner geometry. The complex was applied as an efficient homogeneous catalyst in C-C coupling Heck reaction of arylhalides with olefins such as methylacrylate. Investigation of the catalytic activity of the complex in Heck reaction between arylhalides and olefins showed high yield and selectivity. For example reaction between iodobenzene and...
Catalytic oxidation of sulfides to sulfoxide using manganese(III) complexes with bidentate O,N-donor oxazoline ligand and UHP oxidizing agent
, Article Catalysis Communications ; Volume 10, Issue 2 , 2008 , Pages 196-200 ; 15667367 (ISSN) ; Latifi, R ; Tahsini, L ; Amini, M ; Sharif University of Technology
2008
Abstract
The efficient catalytic systems were investigated for the oxidation of various sulfide by manganese(III)-oxazoline complexes, [Mn(phox)2(MeOH)2]ClO4 and Mn(phox)3 (Hphox = 2-(2′-hydroxyphenyl)oxazoline). These complexes were found efficient catalysts for the oxidation of sulfides with urea hydrogen peroxide (UHP) in short reaction times (5 min) and under mild condition. Sulfoxides were obtained as the main products together with variable amounts of sulfones. The efficiency of the catalytic system was strongly influenced by the nature of solvents and axial ligands so the best yields were achieved in a mixture of methanol: dichloromethane and in the presence of imidazole as co-catalyst. © 2008...
Synthesis, crystal structure and catalytic activity of a novel Mo(VI)-oxazoline complex in highly efficient oxidation of sulfides to sulfoxides by urea hydrogen peroxide
, Article Inorganica Chimica Acta ; Volume 361, Issue 7 , 2008 , Pages 2019-2024 ; 00201693 (ISSN) ; Tahsini, L ; Latifi, R ; Ellern, A ; Woo, L. K ; Sharif University of Technology
Elsevier S.A
2008
Abstract
Novel molybdenum complex, cis-[MoO2(phox)2] has been synthesized and characterized by IR, 1H NMR, elemental analyses (CHN), and X-ray molecular structure determination methods. This complex was found to be an efficient, selective catalyst for the oxidation of various sulfides to sulfoxides with urea hydrogen peroxide (UHP) in excellent yields (100% for diallylsulfide) and short reaction times (20 min) at room temperature. The catalytic system oxidizes diallylsulfide chemoselectively to its corresponding sulfoxide without any over oxidation in double bond. © 2007 Elsevier B.V. All rights reserved
Synthesis, Structure and Catalytic Application of Mn, Fe and Mo Complexes with Schiff base Ligands in the Oxidation of Olefins and Sulfides and Theoretical Mechanistic Studies on the Catalytic Activity of non-Heme Iron and Copper Enzymes
, Ph.D. Dissertation Sharif University of Technology ; Bagherzadeh, Mojtaba (Supervisor)Synthesis, Structure and Catalytic Application of Mn, Fe and Mo Complexes with Schiff base and Oxazoline ligands and Theoretical Mechanistic Studies on the Role of Heme and non-Heme Iron(IV)-Oxo Species in Hydroxylation and Epoxidation Reactions
, Ph.D. Dissertation Sharif University of Technology ; Bagherzadeh, Mojtaba (Supervisor)
Abstract
The first part of this thesis describes the synthesis and characterization of several Mn, Fe and Mo complexes containing tridentate Schiff base and oxazoline ligands and their reactivities as catalysts in the oxidation of organic compounds like olefins and sulfides, as well. The crystal structures of newly prepared cis-dioxo-bis[2-(2′-hydroxyphenyl)-oxazolinato]molybdenum(VI), cis-[MoO2(phox)2] and (N-hydroxyphenyl-salicylidenamine)(acetylacetonato)ethanol iron(III), [FeIII(N-OPh-sal)(acac)EtOH] complexes have been described by X-ray crystallography. Due to the difficulties in the preparation of suitable single crystals of novel...
Catalytic behavior of an iron(III) complex containing an N,O-type bidentate oxazoline ligand for selective oxidation of sulfides
, Article Transition Metal Chemistry ; Volume 41, Issue 1 , 2016 , Pages 97-105 ; 03404285 (ISSN) ; Khaksar, M ; Arab, A ; Masoomi Jahandizi, R ; Bagherzadeh, M ; Boghaei, D. M ; Ellern, A ; Keith Woo, L ; Sharif University of Technology
Springer International Publishing
Abstract
The reaction of Fe(acac)3 and 2-(2′-hydroxyphenyl)oxazoline (Hphox) as a bidentate O,N donor ligand afforded a six-coordinated iron(III) complex [Fe(phox)2(acac)] with distorted octahedral configuration. The complex was isolated as an air-stable crystalline solid and characterized by elemental analysis, FTIR, solution electrical conductivity, and by single-crystal X-ray structure analysis. The structure, electronic properties, and vibrational normal modes of the complex were investigated by DFT. The use of this complex as a catalyst for the oxidation of sulfides to their corresponding sulfoxides using urea hydrogen peroxide as the primary oxidant was investigated. The catalyst shows very...
A novel iron complex containing an N,O-type bidentate oxazoline ligand: Synthesis, X-ray studies, DFT calculations and catalytic activity
, Article Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy ; Vol. 133, issue , Jun , 2014 , p. 432-438 ; Arab, A ; Derakhshandeh, P. G ; Bagherzadeh, M ; Ellern, A ; Woo, L. K ; Sharif University of Technology
Abstract
A five-coordinated Fe(III) complex with the distorted trigonal bipyramidal configuration was synthesized by reactions of FeCl36H2O and 2-(2′-hydroxyphenyl)oxazoline (Hphox) as a bidentate ON donor oxazoline ligand. Complex [Fe(phox)2Cl] was fully characterized, including by single-crystal X-ray structure analysis. DFT calculations were accompanied with experimental results in order to obtain a deeper insight into the electronic structure and vibrational normal modes of complex. Oxidation of sulfides to sulfoxides in one-step was conducted by this complex as catalyst using urea hydrogen peroxide (UHP) in mixture of CH2Cl 2/CH3OH (1:1) under air at room temperature. The results show that using...