- Cyanuric chloride promoted oxidation of sulfides to sulfoxides or sulfones in the presence of hydrogen peroxide
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Aromatic and aliphatic sulfides are readily oxidized to sulfoxides or sulfones in high yield with 35% hydrogen peroxide in the presence of cyanuric chloride (CC) as an efficient activator. The oxidation of sulfides proceeds at room temperature and the corresponding sulfoxides or sulfones was selectively obtained by controlling the amounts of H2O2 and CC. Various sulfides possessing functional groups such as hydroxyl, methoxy, nitrile, aldehyde and olefinic double bond were successfully and selectively oxidized without affecting sensitive functionalities. [image omitted].
- Lakouraj, Moslem Mansour,Abdi, Hamid,Hasantabar, Vahid
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- Ion exchange resin catalyzed selective oxidation of sulfides to sulfoxides using hydrogen peroxide
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An efficient method for the selective oxidation of sulfides to sulfoxides under mild and environmentally safe conditions is achieved using hydrogen peroxide in the presence of Amberlyst 15 and Amberlite IR-400 at room temperature. This procedure can be ap
- Lakouraj, Moslem Mansour,Tajbakhsh, Mahmood,Tashakkorian, Hamed
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- Selective oxidation of sulfides to sulfoxides catalysed by deep eutectic solvent with H2O2
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A Bronsted acidic deep eutectic solvent based on choline chloride and p-toluenesulfonic acid (ChCl/p-TsOH, 1 : 1) was prepared and utilised for the selective oxidation of sulfides with H2O2 as the oxidant. Broad substrate compatibili
- Dai, Dong-Yan,Wang, Liang,Chen, Qun,He, Ming-Yang
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- Alanine/chlorochromic acid/silica gel: An efficient and selective reagent for the oxidation of organic functional groups
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Alanine / chlorochromic acid / silica gel is a new and selective reagent for the efficient oxidation of sulfides, thiols, oximes, and alcohols. Oxidation of sulfides is solvent dependent. In chloroform at room temperature sulfoxides are formed as the major products, while in carbon tetrachloride or under solvent-free conditions solfones are produced in good-to-excellent yields.
- Salehi, Peyman,Khodaei, Mohammad Mehdi,Rostami, Amin
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- A multifunctional Co-based metal-organic framework: heterogeneous catalysis, chemiluminescence sensing and moisture-dependent solvatochromism
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Crystalline materials with multi-catalytic applications are of great value to both fundamental research and practical applications. The platform of metal-organic frameworks (MOFs) is utilized to fabricate a microporous versatile catalyst with high stability. Self-assembly of a flexible ligand, 4-(4-carboxybenzylamino)benzoic acid (H2CBBA), with Co(ii) resulted in a 3D framework, CBBA-Co, with Co3O clusters exposed in the zigzag channels. Upon in situ activation, CBBA-Co exhibited multiple heterogeneous catalytic activities. Theoretical calculations were carried out to give insights into the catalytic process. In addition, CBBA-Co also showed promising potential in optical sensing by virtue of its catalytic activity. The luminol chemiluminescence was greatly enhanced by CBBA-Co, and linear determination of the concentration of H2O2 in the range of 0-30% was established. The successful implementation of CBBA-Co indicates the feasibility and promising future of employing MOFs as an efficient platform for the fabrication and study of multifunctional catalysts, both experimentally and theoretically.
- Xie, Ming-Hua,Wang, Ya,Li, Ruo-Fei,Dong, Peng-Yu,Hou, Gui-Hua,Shao, Rong,Xi, Xin-Guo,Guan, Rong-Feng,Yang, Xiu-Li
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- Magnetic core-shell nanoparticle-supported Sc (III): A novel and robust Lewis acid nanocatalyst for the selective oxidation of sulfides to sulfoxides by H2O2 under solvent-free conditions
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For the first time scandium triflate was supported on modified Fe3O4 magnetic nanoparticles [MNPs-PhSO3-Sc(OTf)2] and characterized using scanning electron microscopy (SEM), inductively coupled plasma analysis (
- Khaledian, Donya,Rostami, Amin,Rouhani, Shamileh
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- Tungstate-exchanged Mg-Al-LDH catalyst: An eco-compatible route for the oxidation of sulfides in aqueous medium
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The catalytic oxidation of sulfides selectively to sulfoxides and/or sulfones is realised for the first time with heterogeneous tungstate-exchanged Mg-Al-LDH catalyst using 30% hydrogen peroxide in aqueous media at a faster rate in quantitative yields at room temperature. The heterogeneous catalyst showed higher activity (TOF) over its homogeneous analogues and other heterogeneous catalysts reported so far. The catalyst is well characterised by various instrumental techniques such as FT-IR spectroscopy, thermal analysis (TGA and DTA), powder XRD and chemical analysis. The catalyst is reused for six cycles with consistent activity and selectivity.
- Choudary,Bharathi,Venkat Reddy,Lakshmi Kantam
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- A SnIV-porphyrin-based metal-organic framework for the selective photo-oxygenation of phenol and sulfides
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A functional tin(IV)-porphyrin derivative was used as a building block to construct a novel 3D porous metal-organic framework (MOF). The MOF is built up from tin(IV)-porphyrin struts linking up Zn atoms and formates joining Sn IV centers. The i
- Xie, Ming-Hua,Yang, Xiu-Li,Zou, Chao,Wu, Chuan-De
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- Efficient and highly selective aqueous oxidation of sulfides to sulfoxides at room temperature catalysed by supported iron oxide nanoparticles on SBA-15
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The present manuscript describes a simple, efficient and environmentally friendly room temperature aqueous catalytic approach to the selective preparation of sulfoxides from sulfides utilising low-loaded supported iron oxide nanoparticles and aqueous hydr
- Rajabi, Fatemeh,Naserian, Sareh,Primo, Ana,Luque, Rafael
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- EFFICENT OXIDATION OF SULFIDES TO THE SULFOXIDES USING A NEW SULFINYLPEROXY INTERMEDIATE GENERATED FROM 2-NITROBENZENESULFINYL CHLORIDE AND SUPEROXIDE
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Various sulfides were found to react with a sulfinylperoxy intermediate generated in situ by the treatment of 2-nitrobenzenesulfinyl chloride with superoxide at -25 deg C in acetonitrile to afford the corresponding sulfoxides selectively in excellent yields together with traceable amount of the sulfones under mild conditions.
- Kim, Yong Hae,Yoon, Dae Chul
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- Enantioselective oxidation of sulfides with hydrogen peroxide catalyzed by vanadium complex of sterically hindered chiral Schiff bases
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Sterically hindered chiral Schiff base ligands 4a-d were prepared from an aldehyde derived from BINOL. The vanadium complexes of the ligands catalyze an efficient, enantioselective H2O2-promoted sulfoxidation of alkyl aryl sulfides, and enantioselectivities as high as 98-99% ee are observed in the sulfoxidation of benzyl aryl sulfides.
- Jeong, Yong-Chul,Choi, Soojin,Hwang, Yao Dong,Ahn, Kwang-Hyun
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- The X-ray structures of sulfoxides
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We have structurally characterized and investigated a range of sulfoxide compounds containing aryl and alkyl substituents. Compounds 1 and 3-6 all crystallize in an orthorhombic space group, where compounds 2 and 7 crystallize in a monoclinic space group.
- Fuller, Amy L.,Aitken, R. Alan,Ryan, Bruce M.,Slawin, Alexandra M. Z.,Woollins, J. Derek
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- Hydrogen-bonding catalysis: Mild and highly chemoselective oxidation of sulfides
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N,N′-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea, employed at only 1 mol% loading, was found to be a very effective catalyst for the oxidation of sulfides with tert-butyl hydroperoxide (TBHP), affording the sulfoxides in high yield, excellent chemoselecti
- Russo, Alessio,Lattanzi, Alessandra
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- Development of a Continuous-Flow Microreactor for Asymmetric Sulfoxidation Using a Biomimetic Manganese Catalyst
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Asymmetric sulfoxidation catalyzed by a biomimetic manganese complex under continuous-flow microreactor is described. The reaction is conducted in microreactor, it can rapidly (4 min) oxidize a wide scope of sulfides with high yield (up to 91%) and excel
- Dai, Wen,Mi, Yuan,Lv, Ying,Chen, Bo,Li, Guosong,Chen, Guangwen,Gao, Shuang
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- HIO3 in the presence of wet SiO2: A mild and efficient reagent for selective oxidation of sulfides to sulfoxides under solvent-free conditions
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In the presence of wet SiO2, HIO3 is highly efficient for the selective oxidation of sulfides to sulfoxides. It may be applied to any type of dialkyl and alkyl aryl sulfides. It develops under solvent-free conditions, and gives high yield in the presence of different functional groups on the sulfide at room temperature.
- Lakouraj,Tajbakhsh,Shirini,Tamami, M. V. Asady
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- Synthesis of benzyl thioether derivatives via N-heterocyclic carbene palladium(II)-catalyzed cross coupling of benzylammonium salts with thiophenols
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A new route to benzyl thioether derivatives has been developed via the N-heterocyclic carbene palladium(II)-catalyzed cross coupling of benzylammonium salts with thiophenols. Under the optimal conditions, different benzylammonium salts could be well toler
- Wang, Tao,Guo, Jiarui,Xu, Yongli,Wang, Xiaobo,Wang, Yan,Feng, Dandan,Liu, Lantao
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- Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes
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Several novel binaphthyl-based chiral hypervalent iodine(III) reagents have been prepared and structurally analysed. Various asymmetric oxidative reactions were applied to evaluate the reactivities and stereoselectivities of those reagents. Moderate to excellent yields were observed; however, very low stereoselectivities were obtained. NMR experiments indicated that these reagents are very easily hydrolysed in either chloroform or DMSO solvents leading to the limited stereoselectivities. It is concluded that the use of chiral ligands is an unsuccessful way to prepare efficient stereoselective iodine(III) reagents.
- Zhang, Huaiyuan,Cormanich, Rodrigo A.,Wirth, Thomas
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supporting information
(2021/12/22)
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- Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst
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We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.
- Zhao, Bin,Hammond, Gerald B.,Xu, Bo
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supporting information
(2021/09/13)
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- Highly efficient and selective aqueous aerobic oxidation of sulfides to sulfoxides or sulfones catalyzed by tungstate-functionalized nanomaterial
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A Br?nsted acidic ionic solid comrising tungstate-functionaized polyorganosiloxane framework (PMO-IL-WO42?) efficiently catalysed aerobic oxidation of sulfides in aqueous medium. The catalyst can selectively produce sulfoxides or sulfones by running the reaction at room temperature or 50 °C, respectively. Because of the ionic liquid-based charged surface containing hydrophobic organic functional groups and hydrophilic sulfonic acid group, the synergestic hydrophobic/hydrophilic and redox effect of PMO-IL-WO42- as water-friendly interfacial nanocatalyst simplifies and enhances the activity and selectivity toward the target sulfoxides or sulfones in water. Moreover, the PMO-IL-WO42- nanocatalyst exhibited outstanding stability and activity and can be recycled eight reaction runs without any significant activity and selectivity loss.
- Luque, Rafael,Rajabi, Fatemeh,Vessally, Esmail,Voskressensky, Leonid
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- Curbed of molybdenum oxido-diperoxido complex on ionic liquid body of mesoporous Bipy-PMO-IL as a promising catalyst for selective sulfide oxidation
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In this work, we introduce a novel bipyridinium ionic liquid bridged periodic mesoporous organosilicas (Bipy-PMOs-IL) which is used as the support to immobilize oxygen-rich Molybdenum (VI)-based oxido-peroxido complex (MoO(O2)2?Bipy-PMO-IL). Several techniques such as Small-angle X-ray scattering (SAXS), low angle XRD, FE-SEM (field emission scanning electron microscope), TEM (transmission electron microscope), N2 adsorption-desorption analyses (BET), atomic absorption spectroscopy (AAS), Fourier-transform infrared spectroscopy (FT-IR) and Energy Dispersive X-Ray (EDS or EDX) were used to characterize this nanomaterial. Also, the catalytic activities of the MoO(O2)2?Bipy-PMO-IL as a hybrid catalyst is tested in the selective oxidation of sulfides in water by using H2O2 (30%) as an eco-friendly and green co-oxidant. The as-prepared novel catalyst shows high to excellent performance under optimum reaction conditions at ambient room temperature. The obtained results in this work show several outstanding advantages, such as green conditions, high product yields, easy work-up, easy preparation and acceptable reusability of the catalyst for at least 5 runs. To study the IL effect in immobilization of Mo-complex, in a comparison study, the MoO(O2)2?Bipy-PMO-IL materials and MoO(O2)2?SBA-15 (with simple SiO2 body, no IL) body were employed for sulfide oxidation. After the treatment, the Mo?Bipy-PMO-IL with IL body in channels was reused for subsequent experiments (5 runs), but in Mo?SBA-15 after second run the yield was decreased dramatically.
- Ahadi, Arefeh,Dugheri, Stefano,Hasanzadeh, Amir,Kavetskyy, Taras,Khaksar, Samad,Mamba, Bhekie B.,Moaser, Azra Ghiasi,Msagati, Titus A.-M.,Rostamnia, Sadegh,Rouhani, Shamila,Shokouhimehr, Mohammadreza
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- Metal-free oxidative coupling of alkyl chlorides with thiols: An efficient access to sulfoxides
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An efficient and step-economical access to sulfoxides from thiols and alkyl halides in the presence of I2O5 and DBU via direct oxidative couplings is described here. It is the first case that combined Williamson sulfide synthesis and subsequent sulfide oxidation into one step manipulation for sulfoxides preparation. This protocol features wide substrate scope, mild and metal-free conditons, the use of naturally abundant starting materials and avoidance of over-oxidation.
- Liu, Qian,Zhao, Xiaoqian,Xu, Feng,Li, Gaoqiang
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- Localized Partitioning of Enantiomers in Solid Samples of Sulfoxides: Importance of Sampling Method in Determination of Enantiopurity
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Localized partitioning of amorphous enantioenriched aryl benzyl sulfoxides in the solid state can lead to substantial variation in enantiopurities, even for sulfoxides which do not show detectable levels of self-disproportionation of enantiomers (SDE) dur
- Flynn, Aaran J.,Ford, Alan,Maguire, Anita R.
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p. 10216 - 10221
(2020/09/09)
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- Method of preparing sulfoxide compounds from benzyl chloride compound and thiophenol by one-step reaction in metal free condition
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The invention discloses a method of preparing sulfoxide compounds from benzyl chloride compound and thiophenol by a one-step reaction in a metal free condition. The method can be used for preparing aseries of sulfoxide compounds in a mild condition by taking benzyl chloride compound and thiophenol as reaction raw materials, iodine pentoxide as an oxidizing agent and 1,8-diazabicycloundecylenic-7-ene as alkali with a high yield. By taking halogenated hydrocarbon and thiol as reactants directly, compared with known and popular methods of generating thioether by halogenated hydrocarbon and thiolunder the action of strong alkali, separating a thioether compound and oxidizing the thioether to synthesize sulfoxide through an oxidizing agent, the reaction steps are shortened to one step from two steps. The middle treatment process of the reaction is few, the atom economy is good, and no transitional metal catalysts take part in the reaction, so that the synthetic cost is low, the reaction condition is mild, and the method opens up a novel and efficient path which is high in atom economy and low in cost for preparing the sulfoxide compounds and has a wide application prospect.
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Paragraph 0014; 0015; 0016; 0017
(2019/04/06)
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- Palladium/PC-Phos-Catalyzed Enantioselective Arylation of General Sulfenate Anions: Scope and Synthetic Applications
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Herein we reported an efficient palladium-catalyzed enantioselective arylation of both alkyl and aryl sulfenate anions to deliver various chiral sulfoxides in good yields (up to 98%) with excellent enantioselectivities (up to 99% ee) by the use of our developed chiral O,P-ligands (PC-Phos). PC-Phos are easily prepared in short steps from inexpensive commercially available starting materials. The single-crystal structure of the PC4/PdCl2 showed that a rarely observed 11-membered ring was formed via the O,P-coordination with the palladium(II) center. The salient features of this method include general substrate scope, ease of scale-up, applicable to the late-stage modification of bioactive compounds, and the synthesis of a marketed medicine Sulindac.
- Wang, Lei,Chen, Mingjie,Zhang, Peichao,Li, Wenbo,Zhang, Junliang
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supporting information
p. 3467 - 3473
(2018/03/13)
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- Nanoarchitecturing of open metal site Cr-MOFs for oxodiperoxo molybdenum complexes [MoO(O2)2@En/MIL-100(Cr)] as promising and bifunctional catalyst for selective thioether oxidation
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In this work, open metal site metal-organic framework of MIL-100(Cr) was selected as a support for the multi-step grafting of molybdenum complexes. The oxodiperoxo molybdenum complexes were coordinated onto the ethylene diamine-decorated MIL-100(Cr) pore
- Rostamnia, Sadegh,Mohsenzad, Farahnaz
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- Synthesis and characterization of sulfamic acid supported on Fe3O4 nanoparticles: A green, versatile and magnetically separable acidic catalyst for oxidation reactions and Knoevenagel condensation
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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.
- Shiri, Lotfi,Narimani, Hojatollah,Kazemi, Mosstafa
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- Nondirected Copper-Catalyzed Sulfoxidations of Benzylic C-H Bonds
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A copper-catalyzed sulfoxidation of benzylic C-H bonds by nondirected oxidative C(sp3)-H activation was developed. The process proceeds via sulfenate anions, which are generated by base-triggered elimination of β-sulfinyl esters and benzyl radicals. The functional group tolerance is high, and the product yields are good.
- Yu, Hao,Li, Zhen,Bolm, Carsten
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supporting information
p. 2076 - 2079
(2018/04/16)
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- A Mild, Efficient and Highly Selective Oxidation of Sulfides to Sulfoxides Catalyzed by Lewis Acid–Urea–Hydrogen Peroxide Complex at Room Temperature
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Alkyl and aryl sulfides were oxidized to the corresponding sulfoxides with urea–hydrogen peroxide (UHP) in the presence of FeCl3 as a Lewis acid catalyst under simple and mild reaction conditions. The protocol is efficient and highly selective
- Azizi, Mojtaba,Maleki, Ali,Hakimpoor, Farahman,Ghalavand, Reza,Garavand, Ali
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p. 2173 - 2177
(2017/07/25)
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- 1,1,2,2-Tetrahydroperoxy-1,2-diphenylethane as new oxidant for chemoselective and catalyst free oxidation of sulfides to sulfoxides and sulfones
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A catalyst free and chemoselective oxidation of sulfides to sulfoxides or sulfones was developed using 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as a new oxidant. This scope has shown the achievement of various sulfoxides and sulfones which were obtained selectively in high yields at room temperature.
- Khosravi, Kaveh,Naserifar, Shirin,Mahmoudi, Boshra,Khalaji, Kobra
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p. 316 - 321
(2017/02/18)
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- Solvent, metal and halogen-free synthesis of sulfoxides by using a recoverable heterogeneous urea-hydrogen peroxide silica-based oxidative catalytic system
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An efficient and green protocol was used for the selective oxidation of sulfides to sulfoxides by using silica sulfuric acid (SSA) as a recoverable heterogeneous solid acid catalyst in the presence of urea-hydrogen peroxide (UHP) under toxic transition me
- Azizi, Mojtaba,Maleki, Ali,Hakimpoor, Farahman
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- Synthesis and characterization of tribenzyl ammonium-tribromide supported on magnetic Fe3O4 nanoparticles: a robust magnetically recoverable catalyst for the oxidative coupling of thiols and oxidation of sulfides
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Abstract: Taking into account the principles of green chemistry, magnetic nanoparticles, especially Fe3O4 nanoparticles, open up a new chapter in modern organic synthesis to inset a fascinating, stupendous and efficient catalytic strategy for facilitating catalyst recovery in various chemical reactions. Inspired by this topic, tribenzyl ammonium-tribromide immobilized on magnetic nanoparticles (Fe3O4–TBA-Br3) as a bromine source was successfully synthesized and its catalytic activity in the oxidative coupling of thiols and oxidation of sulfides was investigated. It is the first report on the use of the immobilized bromine source on Fe3O4 nanoparticles as a nanomagnetic recyclable catalyst for the oxidative coupling of thiols. The nanosolid catalyst could be easily recovered by a simple magnetic separation and reused for several cycles without significant degradation in catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]
- Shiri, Lotfi,Ghorbani-Choghamarani, Arash,Kazemi, Mosstafa
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p. 2707 - 2724
(2017/04/18)
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- Application of sodium titanate nanotubes doped with vanadium (VNaTNT) as a heterogeneous catalyst for oxidation of sulfides at room temperature
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A heterogeneous titanate nanotube (TNT) catalyst containing TiO2, Na, and V has been synthesized and used in the chemoselective oxidation of sulfides to the corresponding sulfoxides in the presence of 30% H2O2 in water. Some of the advantages of our method include excellent yields, heterogeneous conditions, simplicity, compatibility with a variety of functionalities, and ease of isolation of the products. Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, transmission electron microscopy, and N2 adsorption were used for structural and textural characterization of the catalyst (VNaTNT).
- Dadvar, Mohammad Ali,Fazaeli, Razieh
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p. 494 - 501
(2016/04/20)
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- A chemoselective oxidation of sulfides to sulfoxides and sulfones using urea-2,2-dihydroperoxypropane as a novel oxidant
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Background: Sulfoxides and sulfones have been in the center of attention due to their wide range of promises in various approaches. The functional groups presented in these compounds serve as important building blocks in numerous natural, pharmeceutical and agricultural compounds. These deriatives have been prepared through a multitude of routes which were accompanied by several drawbacks. Therefore, there has been an ever-increasing interest to find a new methodology that leads to the production of these compounds via an environmentally benign path bringing about high yields. Recently, gem-dihydroperoxides have attracted much attention due to their oxidizing power and they have been utilized in several oxidation processes. Methods: We carried out a chemoselective oxidation of sulfides to sulfoxides and sulfones on treatment with urea-2,2-dihydroperoxypropane, a solid oxidant composed of equal amounts of 2,2-dihydroperoxypropane and urea, using THF as the solvent under catalyst-free conditions at room temprature. Results: Sulfides possessing a variety of substitutions namely dialkyl, diaryl, ally l and alkyl-aryl were subjected to the optimized reaction conditions and they could successfully afford different amounts of sulfoxides and sulfones depending on the amount of the oxidant utilized. Based on the results, electron-donating groups accelerated the reaction while electron-withdrawing substituents lowered the reactivity. Conclusion: Urea-2,2-dihydroperoxypropane as a solid oxidant which can be stored for several months without any loss in its activity has proved its capability to oxidize sulfides to sulfoxides and sulfones under catalyst-free and mild conditions. This approach is a cost-effective and environmentally benign methodology via which the products have been synthesized in high yields and short reaction times.
- Khosravi, Kaveh,Naserifar, Shirin,Asgari, Atefeh
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p. 749 - 756
(2017/02/05)
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- Method for preparing chiral sulfoxide through catalysis of asymmetric oxidation of thioether
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The invention provides a method for preparing chiral sulfoxide. According to the method, in a mixed solvent, thioether is used as a substrate, a complex produced by chiral tetradentate organic ligand and a metal manganese compound in situ is used as a cat
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Paragraph 0058; 0059; 0060; 0061; 0063
(2016/10/10)
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- One-Pot Sulfoxide Synthesis Exploiting a Sulfinyl-Dication Equivalent Generated from a DABSO/Trimethylsilyl Chloride Sequence
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A one-pot process for the synthesis of unsymmetrical sulfoxides using organometallic nucleophiles is described. Sulfur dioxide, delivered from the surrogate DABSO (DABCO-bis(sulfur dioxide)), acts as the initial electrophile and combines with the first organometallic reagent to generate a sulfinate intermediate. In situ conversion of the sulfinate to a sulfinate silyl ester, using TMS-Cl (trimethylsilyl chloride), generates a second electrophile, allowing addition of a second organometallic reagent. Organolithium or Grignard reagents can be employed, delivering sulfoxides in good to excellent yields.
- Lenstra, Danny C.,Vedovato, Vincent,Ferrer Flegeau, Emmanuel,Maydom, Jonathan,Willis, Michael C.
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p. 2086 - 2089
(2016/06/01)
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- Polymeric ionic liquid nanogel-anchored tungstate anions: A robust catalytic system for oxidation of sulfides to sulfoxides
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A new heterogeneous catalytic system was prepared by immobilization of tungstate ions on a cross-linked poly(ionic liquid) nanogel. The solid nanogel was easily synthesized by a surfactant-less method. The resulting catalyst was highly active in selective
- Pourjavadi, Ali,Nazari-Chamazkoti, Mojtaba,Hosseini, Seyed Hassan
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p. 1348 - 1354
(2015/02/19)
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- Tetrabutylammonium tribromide impregnated MCM-48 as a heterogeneous catalyst for selective oxidation of sulfides
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We report here tetrabutylammonium tribromide supported on MCM-48 as a highly efficient heterogeneous catalyst for the selective oxidation of sulfides, in ethanolic medium using hydrogen peroxide as an oxidant. The aforementioned oxidation reactions were found to proceed rapidly (20 min) and in good yield (85-99%) (17 examples). The oxidation products were characterized by 1H NMR, 13C NMR and elemental analysis. The catalytic properties were analysed by TEM, XRD and BET-surface area measurement. No over-oxidation of the substrates was observed (analysed by GC), and the catalyst was effectively recycled for five consecutive cycles without any significant loss in its catalytic activity.
- Gogoi, Prasanta,Hazarika, Sukanya,Barman, Pranjit
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p. 38044 - 38047
(2015/06/30)
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- Photosensitized oxidation of aryl benzyl sulfoxides. Evidence for nucleophilic assistance to the c-s bond cleavage of aryl benzyl sulfoxide radical cations
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The radical cations of a series of aryl benzyl sulfoxides (4-X-C6H4CH2SOC6H4Y+?) have been generated by photochemical oxidation of the parent sulfoxides sensitized by 3-cyano-N-methylquinolinium perchlorate (3-CN-NMQ+ClO4-). Steady-state photolysis experiments showed the prevailing formation of benzylic products deriving from the C-S fragmentation in the radical cations, together with sulfur-containing products. Formation of sulfoxide radical cations was unequivocally established by laser flash photolysis experiments showing the absorption bands of 3-CN-NMQ? (λmax = 390 nm) and of the radical cations (λmax = 500-620 nm). The decay rate constants of radical cations, determined by LFP experiments, decrease by increasing the electron-donating power of the arylsulfinyl Y substituent and to a smaller extent by increasing the electron-withdrawing power of the benzylic X substituent. A solvent nucleophilic assistance to the C-S bond cleavage has been suggested, supported by the comparison of substituent effects on the same process occurring in aryl tert-butyl sulfoxide radical cations. DFT calculations, performed to determine the bond dissociation free energy in the radical cations, the transition state energies associated with the unimolecular C-S bond cleavage, and the charge and spin delocalized on their structures, were also useful to endorse the nucleophilic assistance to the C-S scission.
- Del Giacco, Tiziana,Lanzalunga, Osvaldo,Lapi, Andrea,Mazzonna, Marco,Mencarelli, Paolo
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p. 2310 - 2318
(2015/09/08)
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- Nickel(II), copper(II), and cobalt(II) complexes derived from a new unsymmetrical ONS donor schiff base ligand: Synthesis, characterization, crystal structure, and catalytic activities
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A series of Ni(II), Cu(II), and Co(II) complexes, ML2, of a new thioether containing ONS donors have been synthesized, where L = deprotonated Schiff base. The analytical, spectral (FTIR,1H NMR, UV–vis), conductivity, and magnetic stu
- Kalita, Mukul,Gogoi, Prasanta,Barman, Pranjit,Sarma, Bipul
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p. 2445 - 2454
(2014/10/15)
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- Palladium(II)-catalyzed ortho -olefination of arenes applying sulfoxides as remote directing groups
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A novel palladium-catalyzed ortho-C(sp2)-H olefination protocol has been developed by the use of sulfoxide as the directing group. Importantly, relatively remote coordination can be accessed to achieve the ortho olefination of benzyl, 2-arylethyl, and 3-arylpropenyl sulfoxide substrates, and the olefinated sulfoxide can be easily transformed to other functionalities.
- Wang, Binjie,Shen, Chuang,Yao, Jinzhong,Yin, Hong,Zhang, Yuhong
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supporting information
p. 46 - 49
(2014/01/23)
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- Synthesis of sulfur-bridged polycycles via Pd-catalyzed dehydrogenative cyclization
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A general approach to sulfur-bridged polycycles by palladium-catalyzed double C(sp2)-H bond oxidative cyclization is presented. This protocol afforded diverse sulfur-bridged five-, six-, and seven-membered polycycles in moderate to good yields with a tolerance for a wide variety of functional groups. A sulfide-bridged six-membered pyrene-thienoacene compound was synthesized readily using this method, and excellent performance for photoluminescence quantum yield was observed.
- Wang, Binjie,Liu, Yue,Lin, Cong,Xu, Yiming,Liu, Zhanxiang,Zhang, Yuhong
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supporting information
p. 4574 - 4577
(2015/01/08)
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- Enantioselective oxidation of sulfides with H2O2 catalyzed by a pre-formed manganese complex
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A facile and environmentally friendly method is presented for the asymmetric oxidation of sulfides with H2O2, utilizing a pre-formed manganese complex. Just in the presence of a low catalytic amount of carboxylic acid (CA), a variety of sulfide substrates, including aryl alkyl, aryl benzyl and cyclic sulfides, reacted to form chiral sulfoxides in high yields (up to 95%) and excellent enantioselectivities (>99% ee) under mild conditions. Moreover, the practical utility of the method has been demonstrated by the synthesis of esomeprazole and albendazole sulfoxide (ABZO).
- Dai, Wen,Li, Guosong,Wang, Lianyue,Chen, Bo,Shang, Sensen,Lv, Ying,Gao, Shuang
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p. 46545 - 46554
(2014/12/10)
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- Nano-rod catalysts: Building MOF bottles (MIL-101 family as heterogeneous single-site catalysts) around vanadium oxide ships
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Porous materials based on chromium (III) terephthalate metal organic frameworks (Cr-MIL(101)) and their new composites with vanadium oxide has emerged as a potential catalyst because of its high specific surface area, tunable pore size, and unique structure. The structural and textural characterization of V@MIL(101) were done using FTIR, X-ray diffraction, N 2 adsorption-desorption, and TEM. XRD and adsorption-desorption analysis shows that the mesostructure of MIL-101 remains intact after vanadium oxide modifications, while spectral technique show the successful immobilizing of the neat vanadium oxide inside the MIL-101 cavities. These new catalysts were found to be highly effective for selective oxidation of sulfides to sulfoxides and sulfones with H2O2 at room temperature and the 4.2% V@MIL(101) catalyst showed the highest activity. The PW12@MCF im heterogeneous system showed high catalytic oxidative activity in the treatment of commodity gasoline.
- Fazaeli, Razieh,Aliyan, Hamid,Moghadam, Majid,Masoudinia, Mona
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- Titanium-salan-catalyzed asymmetric sulfoxidations with H2O 2: Design of more versatile catalysts
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Titanium-salan complexes with 3,3'-diphenyl substituents in the salicylidene rings of the salan ligand are efficient sulfoxidation catalysts, capable of catalyzing the asymmetric oxidation of bulky aryl benzyl sulfides with H2O2 with good to high enantioselectivities. In this paper, substituent effects on titanium-salan-catalyzed enantioselective oxidation of sulfides to sulfoxides have been systematically investigated. Titanium-salan catalysts with halogen substituents at the 5,5'-positions (3,3'-H2dihydrogen substituted) have been found to catalyze the oxidation of both bulky aryl benzyl sulfides and small alkyl phenyl sulfides with good to high enantioselectivities. Kinetic data witness a direct attack of the sulfide to the electrophilic active oxygen species; a consistent reaction mechanism is proposed. Copyright 2013 John Wiley & Sons, Ltd. Titanium-salan complexes with halogen substituents at the 5,5'-positions are versatile catalysts for the oxidation of both bulky aryl benzyl sulfides and small alkyl phenyl sulfides, demonstrating good to high chemoselectivity (up to 92 %) and enantioselectivity (up to 93 % ee). Copyright
- Talsi, Evgenii P.,Bryliakov, Konstantin P.
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p. 239 - 244
(2013/06/04)
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- Tungstate based poly(ionic liquid) entrapped magnetic nanoparticles: A robust oxidation catalyst
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A novel magnetically recoverable oxidation catalyst was prepared in which magnetic nanoparticles were entrapped in a tungstate functionalized poly(ionic liquid) matrix. Using H2O2 as an oxidant, a wide range of substrates including alcohols, sulfides and olefins were selectively oxidized with excellent yields. The resulting catalyst was characterized by FTIR, TGA, SEM, TEM, XRD, XRF, CHN, vibrating sample magnetometer (VSM) and atomic adsorption spectroscopy (AAS). The catalyst can be readily recovered and reused at least ten times under the described reaction conditions without significant loss of reactivity.
- Pourjavadi, Ali,Hosseini, Seyed Hassan,Matloubi Moghaddam, Firouz,Koushki Foroushani, Behzad,Bennett, Craig
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p. 2913 - 2919
(2013/10/08)
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- Asymmetric oxidation catalysis by a porphyrin-inspired manganese complex: Highly enantioselective sulfoxidation with a wide substrate scope
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The first genuinely promising porphyrin-inspired manganese-catalyzed asymmetric sulfoxidation method using hydrogen peroxide has been successfully developed, allowing for rapidly oxidizing (0.5-1.0 h) a wide variety of sulfides in high yields with excellent enantioselectivities (up to >99% ee).
- Dai, Wen,Li, Jun,Chen, Bo,Li, Guosong,Lv, Ying,Wang, Lianyue,Gao, Shuang
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supporting information
p. 5658 - 5661
(2013/12/04)
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- Investigation of steric and electronic effects in the copper-catalysed asymmetric oxidation of sulfides
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Steric and electronic effects in the copper-catalysed asymmetric oxidation of aryl benzyl, aryl alkyl and alkyl benzyl sulfides have been investigated. The presence of an aryl group directly attached to the sulfur is essential to afford sulfoxides with high enantioselectivities, with up to 97% ee for 2-naphthyl benzyl sulfoxide, the highest enantioselectivity achieved to date for copper-catalysed asymmetric sulfoxidation. In contrast, the benzyl substituent can be replaced by sterically comparable groups with no effect on enantioselectivity. Copper-mediated oxidation of substituted aryl benzyl sulfides display modest steric and electronic effects resulting in comparable or lower enantioselectivities to those obtained with the unsubstituted benzyl phenyl sulfide.
- O'Mahony, Graham E.,Eccles, Kevin S.,Morrison, Robin E.,Ford, Alan,Lawrence, Simon E.,Maguire, Anita R.
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supporting information
p. 10168 - 10184
(2013/11/06)
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- Sulfenate substitution as a complement and alternative to sulfoxidation in the diastereoselective preparation of chiral β-substituted β-amino sulfoxides
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Building from a previous communication, the reaction of sulfenate anions with chiral N-Boc-protected β-substituted β-amino iodides was evaluated as a conceptually different synthetic approach to chiral β-substituted β-amino sulfoxides. Using arenesulfenat
- S?derman, Stefan C.,Schwan, Adrian L.
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p. 1638 - 1649
(2013/03/28)
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- Host (aluminum incorporated mesocellulous silica foam (Al-MCF))-guest (tungsten polyoxometalate) nanocomposite material: An efficient and reusable catalyst for selective oxidation of sulfides to sulfoxides and sulfones
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A green, efficient and selective approach for the oxidation of sulfides to sulfoxides and sulfones with H2O2 at room temperature is reported. The reaction is performed in the presence of tungstophosphoric acid (PW12) supported on an aluminum incorporated mesocellulous silica foam (Al-MCF) (via both: the impregnation and encapsulation methods), as heterogeneous and reusable catalysts. The structural and textural characterizations of these catalysts were done using FTIR, X-ray diffraction, N2 adsorption-desorption and TEM.
- Fazaeli, Razieh,Aliyan, Hamid,Ahmadi, Mohammad Ali,Hashemian, Saeedeh
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- Highly efficient selective oxygenation of sulfides to sulfoxides by oxalic acid dihydrate in the presence of h2o2
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A highly efficient method for the oxidation of sulfides to sulfoxides using oxalic acid dihydrate in the presence of hydrogen peroxide has been developed. A versatile procedure for the oxidation of sulfides to sulfoxides without any over-oxidation to sulf
- Mokhtary, Masoud,Qandalee, Mohammad,Niaki, Masoumeh Rastegar
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experimental part
p. 863 - 868
(2012/07/14)
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- Copper-catalyzed asymmetric oxidation of sulfides
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Copper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of th
- O'Mahony, Graham E.,Ford, Alan,Maguire, Anita R.
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body text
p. 3288 - 3296
(2012/05/20)
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- A new methodology for the oxidation of sulfides with Fe(III) catalysts
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A variety of sulfides were converted to the corresponding sulfoxide derivatives with 70% t-BuOOH (water) as the oxidant in the presence of catalytic quantity of Fe2(SO4)3. The method described has a wide range of applicati
- Chakraborty, Debashis,Malik, Payal,Goda, Vinod Kumar
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experimental part
p. 21 - 26
(2012/03/11)
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- Catalytic enantioselective oxidation of bulky alkyl aryl thioethers with H2O2 over titanium-salan catalysts
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A simple and efficient catalytic procedure for the oxidation of bulky (preferably aryl benzyl substituted) thioethers with hydrogen peroxide in good to high yields and enantioselectivities (up to 98.5%ee) is reported. The high optical yields are achieved in a tandem stereoconvergent enantioselective oxidation and kinetic resolution process. A reasonable balance between the sulfoxide yield and enantioselectivity could be found by varying the concentration and temperature. An improved synthesis of the titanium-salan catalysts for the preparation of a more stereoselective catalyst is reported.
- Bryliakov, Konstantin P.,Talsi, Evgenii P.
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experimental part
p. 4693 - 4698
(2011/10/03)
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- Silver nitrate catalyzed oxidation of sulfides
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A variety of sulfides were converted into the corresponding sulfoxide derivatives with 70% tert-butyl hydroperoxide in water as the oxidant in the presence of catalytic quantity of silver nitrate. The method described has a wide range of application, does not involve cumbersome workup, exhibits chemoselectivity, and proceeds under mild reaction conditions, and the resulting products are obtained in good yields within a reasonable time. Georg Thieme Verlag Stuttgart New York.
- Das, Rima,Chakraborty, Debashis
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experimental part
p. 277 - 280
(2011/03/18)
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- Organocatalytic asymmetric synthesis of sulfoxides from sulfenic acid anions mediated by a cinchona -derived phase-transfer reagent
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Preliminary results concerning a conceptually novel route to chiral sulfoxides based on the asymmetric alkylation of sulfenate salts with alkyl halides mediated by a chiral phase-transfer catalyst are described. As a representative example, o-anisyl methyl sulfoxide was produced in 96% yield and with an enantiomeric excess of 58% using commercial cinchonidinium derivative 2a.
- Gelat, Fabien,Jayashankaran, Jayadevan,Lohier, Jean-Francois,Gaumont, Annie-Claude,Perrio, Stephane
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p. 3170 - 3173
(2011/08/06)
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- Oxidation of sulfides to sulfoxides with H2O2/HNO3 reagent system
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Selective oxidation of sulfides to sulfoxides is achieved by H2O2 using HNO3 as the promotor. Aromatic and aliphatic sulfides are oxidized to sulfoxides in excellent yields and short reaction times. Different functional groups including C-C double bond, ester, ketone, acetal, alcohol, and oxime groups are tolerated under this reaction condition.
- Khodaei, Mohammad Mehdi,Bahrami, Kiumars,Arabi, Mehdi Sheikh
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experimental part
p. 83 - 88
(2010/10/20)
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- TAPC-promoted oxidation of sulfides and deoxygenation of sulfoxides
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Figure presented. 1,3,5-Triazo-2,4,6-triphosphorine-2,2,4,4,6,6- tetrachloride (TAPC) was found to be an efficient promoter for the oxidation of sulfides and deoxygenation of sulfoxides. Excellent yields, short reaction time, easy and quick isolation of the products, solvent-free process, and excellent chemoselectivity are the main advantages of this procedure.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Sheikh Arabi, Mehdi
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supporting information; experimental part
p. 6208 - 6213
(2010/11/04)
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- Cu(II)-catalyzed oxidation of sulfides
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A variety of sulfides and disulfides were converted into the corresponding sulfoxide derivatives with 70% t-BuOOH (water) as the oxidant in the presence of catalytic quantity of CuBr2. The method described does not involve cumbersome work-up, has wide range of applicabilities, exhibits chemoselectivity, and proceeds under mild reaction conditions, and the resulting products are obtained in good yields within reasonable time.
- Das, Rima,Chakraborty, Debashis
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scheme or table
p. 6255 - 6258
(2011/01/04)
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