cas 945-51-7, Phenyl sulfoxide | Articles data

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Stereoselective oxidation of thiacalix[4]arenes with the NaNO 3/CF3COOH system
A series of alkyl substituted thiacalix[4]arene derivatives (being conformationally mobile or immobilised in the cone conformation) was used as the starting point for this study. It was demonstrated that the NaNO 3/CF3COOH system can
Lhoták, Pavel,Morávek, Ji?í,?mejkal, Tomá?,Stibor, Ivan,Sykora, Jan
p. 7333 - 7336
(2003)
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New oxovanadium and dioxomolybdenum complexes as catalysts for sulfoxidation: experimental and theoretical investigations of E and Z isomers of ONO tridentate Schiff base ligand
A new ONO-tridentate Schiff base ligand (H2L) derived by the condensation of nicotinic hydrazide with 5-chlorosalicylaldehyde has been prepared and characterized by combustion analysis (CHN), FT-IR and multinuclear (1H and 13C) NMR spectroscopy. The crystalline nature and molecular structure of the ligand were confirmed by single-crystal X-ray diffraction analysis. Furthermore, the optimized structural parameters of the four possible configurations of the ligand including Z and E stereoisomers each containing two tautomeric forms (enol and keto) have also been investigated. The theoretical parameters were calculated by performing the DFT method using the B3LYP/Def2-TZVP level of theory. In addition to this, dioxomolybdenum(VI) (MoO2L) and oxovanadium(V) (VOL) complexes with the entitled Schiff base ligand have also been prepared and characterized by different techniques. Then, the catalytic efficiencies of synthesized VOL and MoO2L complexes were also explored for the oxidation of sulfides using 30% aqueous H2O2 as a source of oxygen. These homogeneous catalysts showed excellent catalytic activities in the oxidation of both aromatic and aliphatic sulfides.
Kargar, Hadi,Moghimi, Atefeh,Fallah-Mehrjardi, Mehdi,Behjatmanesh-Ardakani, Reza,Rudbari, Hadi Amiri,Munawar, Khurram Shahzad
p. 22 - 36
(2021/06/23)

Oxovanadium and dioxomolybdenum complexes: synthesis, crystal structure, spectroscopic characterization and applications as homogeneous catalysts in sulfoxidation
New oxovanadium and dioxomolybdenum Schiff base complexes, [VO(L)(OCH3)] n and [MoO2(L)(CH3OH)], were synthesized by treating an ONO donor Schiff base (H2L) derived by condensation of 3-ethoxysalicylaldehyde and nicotinic hydrazide with oxo and dioxo acetylacetonate salts of vanadium and molybdenum (VO(acac)2 and MoO2(acac)2), respectively. The synthesized ligand and complexes were characterized by FTIR, multinuclear (1H, 13C) NMR, elemental and single crystal X-ray diffraction analysis. In both complexes, the geometry around the central metal ions was distorted octahedral as revealed by diffraction studies. Theoretical calculations of the synthesized compounds were carried out by DFT at B3LYP/Def2-TZVP level of theory, which showed good correlation with the experimental results. Moreover, the catalytic efficiency of both complexes was investigated by oxidizing aryl and alkyl sulfides in the presence of 30% H2O2 in ethanol.
Kargar, Hadi,Kaka-Naeini, Azar,Fallah-Mehrjardi, Mehdi,Behjatmanesh-Ardakani, Reza,Amiri Rudbari, Hadi,Munawar, Khurram Shahzad
p. 1563 - 1583
(2021/05/11)

Sulfoxide and Sulfone Synthesis via Electrochemical Oxidation of Sulfides
The oxidation of diaryl sulfides and aryl alkyl sulfides to the corresponding sulfoxides and sulfones under electrochemical conditions is reported. Sulfoxides are selectively obtained in good yield under a constant current of 5 mA for 10 h in DMF, while sulfones are formed as the major product under a constant current of 10 or 20 mA for 10 h in MeOH. The oxygen of both the sulfoxide and sulfone function is derived from water.
Lee, Sunwoo,Park, Jin Kyu
p. 13790 - 13799
(2021/10/12)

Electrochemical Scalable Sulfoxidation of Sulfides with Molecular Oxygen and Water
An efficient and chemoselective synthesis of sulfoxides through the electrooxidation of sulfides has been well developed. This protocol takes advantage of electricity as the terminal oxidant and of molecular oxygen and water as the oxygen atom sources. A variety of structurally diverse sulfoxide compounds are assembled in moderate to excellent yields. The scaled-up reactions at 6–20 mmol show the good practicability and application potential of this methodology. A possible free radical mechanism has been proposed to rationalize the reaction procedure.
Cheng, Zhen,Gao, Xinglian,Yao, Lingling,Wei, Zhaoxin,Qin, Guohui,Zhang, Yonghong,Wang, Bin,Xia, Yu,Abdukader, Ablimit,Xue, Fei,Jin, Weiwei,Liu, Chenjiang
p. 3743 - 3747
(2021/07/26)

Organocatalytic sulfoxidation
Treatment of a sulfide with a catalytic amount of a 1,3-diketone in the presence of silica sulfuric acid as a co-catalyst and hydrogen peroxide (50% aq) as the stoichiometric oxidant leads to the corresponding sulfoxide product. The reaction is effective for diaryl, aryl-alkyl and dialkyl sulfides and is tolerant of oxidisable and acid sensitive functional groups. Investigations have shown that the tris-peroxide 2, formed on reaction of pentane-2,4-dione with hydrogen peroxide under acidic reaction conditions, can oxidise two equivalents of sulfide using the exocyclic peroxide groups whereas the endocyclic peroxide remains intact. Calculations provide a mechanism consistent with experimental observations and suggest the reaction proceeds via an initial acid catalysed ring opening of a protonated tris-peroxide prior to oxygen transfer to a sulfur nucleophile.
Davidson, Stuart C.,Gomes, Gabriel dos Passos,Kuhn, Leah R.,Alabugin, Igor V.,Kennedy, Alan R.,Tomkinson, Nicholas C.O.
(2020/12/07)

Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst
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
supporting information

(2021/09/13)

Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide
A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.
Cao, Zhong-Yan,Li, Xiaolong,Lu, Hao,Wang, Panpan,Wang, Shengqiang,Xu, Xiaobo,Yan, Leyu,Yang, A-Xiu
supporting information
p. 8691 - 8695
(2021/10/22)

Synthesis method of diphenyl sulfoxide
The invention discloses a synthesis method of diphenyl sulfoxide. The synthesis method of the diphenyl sulfoxide comprises the following steps: 1) adding pure benzene and aluminum trichloride into a reactor, heating to 35 to 45 DEG C under stirring, adding sulfoxide chloride dropwise, continuously stirring and completely reacting at 30 to 60 DEG C to obtain a benzene solution of the diphenyl sulfoxide; and 2) adding the benzene solution of the diphenyl sulfoxide into water dropwise, performing hydrolysis, controlling the dropwise adding temperature to be less than 70 DEG C, and performing treatment and purification after complete hydrolysis to obtain the product diphenyl sulfoxide. The synthesis method of the diphenyl sulfoxide has the advantages of cheap and easily available raw materials, mild reaction condition, low energy consumption, simple process structure, easiness in operation and the like.
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Paragraph 0022; 0029-0050

(2020/01/25)

Selective and solventless oxidation of organic sulfides and alcohols using new supported molybdenum (VI) complex in microwave and conventional methods
A new dioxo-molybdenum (VI) complex supported on functionalized Merrifield resin (MR-Mo) has been synthesized and characterized by elemental, scanning electron mcroscopy, energy-dispersive X-ray analysis, TGA, Brunauer–Emmett–Teller method, powder-X-ray d
Das, Siva Prasad,Boruah, Jeena Jyoti
(2020/06/03)

Preparation and characterization of Cu (II) Schiff base complex functionalized boehmite nanoparticles and its application as an effective catalyst for oxidation of sulfides and thiols
The synthesis, characterization, and evaluation of a Schiff base Cu (II) complex functionalized boehmite nanoparticles (Cu-complex-boehmite) as a new catalyst for oxidation of sulfides and thiols in the presence of hydrogen peroxide with complete selectivity and high conversion under solvent-free and mild reaction conditions were reported. Characterization of the catalyst was performed with various physicochemical methods. This effective catalyst was evaluated in terms of activity and reusability. It indicated high catalytic activity, good recoverability and reusability, and supplied the corresponding products in high yields and short reaction times. In addition, it shows notable advantages such as simplicity of operation, heterogeneous nature, easy work up, and it could be used at least eight times with no significant loss of its activity.
Khodaei, Mohammad Mehdi,Alizadeh, Abdolhamid,Afshar Hezarkhani, Hadis
(2019/11/20)

Grignard-Reagent-Promoted Desulfonylation/Intramolecular Coupling for the Synthesis of 2-(1-Fluorovinyl)pyridines
A novel process involving Grignard-reagent-promoted desulfonylation/intramolecular coupling of readily available α-fluoro-α,β-unsaturated-(2-pyridyl)sulfones was realized that provided a series of polysubstituted 2-(1-fluorovinyl)pyridines in good yields. The intrinsic coordination between pyridine and Mg(II) along with the "negative fluorine effect"of the substrates should play the key role for the smooth transformation in the absence of transition-metal catalysts.
Jiang, Gaoxi,Kang, Lei,Qian, Jinlong,Yang, Huameng,Zhang, Jinlong
supporting information
p. 9118 - 9122
(2020/12/02)

Diastereoisomerically pure, (S)-O-1,2-O-isopropyli dene-(5-O-α-d-glucofuranosyl) t-butanesulfinate: Synthesis, crystal structure, absolute configuration and reactivity
The reaction of t-butylmagnesium chlorides with diastereomerically pure (R)-1,2-Oisopropylidene-3,5-O-sulfinyl-α-d-glucofuranose (R)-4 was found to be stopped at the stage of the corresponding, diastereoisomerically pure 1,2-O-isopropylidene-(5-O-α-d-glucofuranosyl) t-butanesulfinate (S)-10 for which the crystal structure and the (S)-absolute configuration was determined by X-ray crystallography. Comparison of the absolute configurations of the starting sulfite (R)-4, and t-butanesulfinate (S)-10 (which crystallizes in the orthorhombic system, space group P212121, with the single compound molecule present in the asymmetric unit), clearly indicates that the reaction of nucleophilic substitution at the stereogenic sulfur atom in the sulfite (R)-4 occurs with the full inversion of configuration via the trigonal bipyramidal sulfurane intermediate 4c in which both the entering and leaving groups are located in apical positions.
B?aszczyk, Jaros?aw,Bujnicki, Bogdan,Chmielewski, Marek,Drabowicz, Józef
(2020/09/16)

Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides
A highly chemoselective, efficient and nano-Pd catalyzed protocol for the rapid construction of sulfoxides and sulfones via the oxidation of symmetrical and unsymmetrical sulfides using H2O2 as an oxidant has been developed, respectively. The ready availability of starting materials, easy recovery and reutilization of the catalyst, wide substrate scope, and high yields make this protocol an attractive alternative. The process also involves the metal-free and microwave-promoted synthesis of symmetrical diarylsulfides, and FeCl3-mediated preparation of symmetrical diaryldisulfides through the reaction of arenediazonium tetrafluoroborates with Na2S·9H2O as a sulfur source. In addition, unsymmetrical sulfides were generated via the K2CO3-mediated reaction of arenediazonium tetrafluoroborates with symmetrical disulfides.
Li, Xing,Du, Jia,Zhang, Yongli,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
p. 3048 - 3055
(2019/03/21)

Fe3O4?BNPs?SiO2-SO3H as a highly chemoselective heterogeneous magnetic nanocatalyst for the oxidation of sulfides to sulfoxides or sulfones
To achieve green chemistry goals and also to reduce the cost of catalysts as well as to avoid producing toxic wastes and show the importance of separation and recycling of catalysts from the reaction medium, in this work, we describe the preparation and characterization of magnetic acidic boehmite nanoparticles as a heterogeneous catalyst, which is called Fe3O4?BNPs?SiO2-SO3H. This catalyst works efficiently in the selective oxidation of sulfides to sulfoxides or sulfones in the presence of H2O2 as a green oxidant. It can easily be separated from the reaction medium by using an external magnet and it was recycled 6 times without loss of magnetic catalytic properties.
Ghanbari Kermanshahi, Mohammad,Bahrami, Kiumars
p. 36103 - 36112
(2019/11/20)

Efficient Liquid-Assisted Grinding Selective Aqueous Oxidation of Sulfides Using Supported Heteropolyacid Catalysts
The present work reports the preparation of 40MoAl200 and its full characterization using a number of analytical techniques (XRD, TEM, TGA, BET, EDX). Liquid-assisted ball milling proved to be a key tool to achieve both the best efficiency of 40MoAl200 as a novel Keggin type catalyst in the selective sulfoxidation reaction and also for succeeding in its effective recovery and reuse. In addition, the liquid assisted grinding process was studied in detail evaluating the influence of different parameters such as frequency of rotation (rpm), number and size of the stainless steel balls used and reaction time. The use of aqueous hydrogen peroxide is essential as water proved to exert a crucial role to improve both yields and selectivity towards sulfoxide formation. The procedure was representatively extended to a number of substrates with the possibility to extend the scope of the system to produce sulfoxides in high yields (up to 95 %) and satisfactory selectivities (up to 80 %). The catalyst proved to be recoverable and reusable under the optimized reaction conditions.
Trombettoni, Valeria,Franco, Ana,Sathicq, A. Gabriel,Len, Christophe,Romanelli, Gustavo P.,Vaccaro, Luigi,Luque, Rafael
p. 2537 - 2545
(2019/04/30)

Water-soluble polymer anchored peroxotitanates as environmentally clean and recyclable catalysts for mild and selective oxidation of sulfides with H2O2 in water
Anchoring of peroxotitanium (pTi) species to linear water-soluble acrylic acid based polymers, poly(sodium acrylate) (PA) and poly(sodium methacrylate) (PMA) led to the successful synthesis of a pair of new, water-tolerant and recyclable catalysts of the type [Ti2(O2)2O2(OH)2]4-—L (L = PA or PMA), highly effective in chemoselective sulfoxidation of organic sulfides with 30% H2O2 in aqueous medium at ambient temperature. The catalytic protocol is high yielding (TOF up to 11,280 h?1), operationally simple as well as environmentally clean and safe, being free from halide, or any other toxic auxiliaries. The catalysts are sufficiently stable to afford easy recyclability for at least 10 consecutive reaction cycles of sulfoxidation with consistent activity selectivity profile. Oxidation of dibenzothiophene (DBT) to respective high purity sulfoxide or sulfone could also be accomplished using the same catalysts by variation of reaction conditions.
Ahmed, Kabirun,Saikia, Gangutri,Paul, Sivangi,Baruah, Satyajit Dey,Talukdar, Hiya,Sharma, Mitu,Islam, Nashreen S.
(2019/10/02)

Catalyst-free visible-light-initiated oxidative coupling of aryldiazo sulfones with thiols leading to unsymmetrical sulfoxides in air
A facile and efficient visible-light-driven method has been developed to construct sulfoxides via oxidative coupling of aryldiazo sulfones with thiols using the O2 in air as the oxidant. This reaction could be performed at room temperature under catalyst- and additive-free conditions. The present methodology offers a mild and environmentally benign approach to obtain a library of sulfoxides in good yields with favorable functional group tolerance.
Liu, Qishun,Wang, Leilei,Yue, Huilan,Li, Jiang-Sheng,Luo, Zidan,Wei, Wei
supporting information
p. 1609 - 1613
(2019/04/08)

Method for preparing visible light promoted asymmetric sulfoxide compound
The invention belongs to the field of organic synthetic chemistry, particularly relates to a preparation method of an asymmetric sulfoxide compound, and particularly discloses a method for synthesizing the asymmetric sulfoxide compound based on visible light catalysis. A compound shown in the formula I and a compound shown in the formula II are added to a reactor, a mixture of an organic solvent and water is added as a reaction solvent, the reactor is connected to air, under the irradiation of visible light, a reaction at a room temperature is performed for 16-40 hours; and after a detection reaction of a TLC thin layer chromatography plate is completed, pure water is added, then the extraction is performed, extract liquid is combined and dried, the extract liquid is concentrated and purified to obtain a compound shown in the formula III, and the compound is the asymmetric sulfoxide compound. The reaction conditions are mild, energy is clean, a strong oxidant is not needed, the safetyof the reaction is improved, the pollution caused by using a metal reagent is avoided, and the reaction cost is saved.
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Paragraph 0048; 0049

(2019/06/11)

A highly efficient reusable homogeneous copper catalyst for the selective aerobic oxygenation sulfides to sulfoxides
Readily available copper showed efficient activity and great selectivity for the homogeneous catalysis of oxidation of sulfides to sulfoxides using molecular oxygen as the oxidant. The reaction proceeds under mild conditions in the presence of a catalytic amount of TEMPO. Importantly, the catalysts could be conveniently recovered and reused. And this methodology was proved to be applicable for the transformation of various aromatic and aliphatic sulfides into the corresponding sulfoxides with high conversion and high selectivity.
Ren, Cheng,Fang, Runxing,Yu, Xiaochun,Wang, Shun
supporting information
p. 982 - 986
(2018/02/13)

Synthesis of new oxido-vanadium complexes: Catalytic properties and cytotoxicity
Reaction of 2,3-dihydroxy benzaldehyde with 2-({2-amino phenyl}diazenyl)phenol afforded the ligand 3-(2-(2-hydroxyphenyl)diazenyl)- 4-alkylphenyliminomethyl)benzene-1,2-diol. Reaction of H2L with VOSO4. 5H2O gave the oxido-vanadium(IV) complexes [(L)VO], which exhibited a quasi-reversible oxidative cyclic voltammetric response in a V(IV)/V(V) oxidative process. The complexes act as catalysts in the oxidation of organic thioethers and bromination of phenol. Their cytotoxic properties were examined for three cancer cell lines.
Das, Uttam,Pattanayak, Poulami,Santra, Manas Kumar,Chattopadhyay, Surajit
p. 57 - 62
(2018/02/28)

Sandwich type polyoxometalates encapsulated into the mesoporous material: Synthesis, characterization and catalytic application in the selective oxidation of sulfides
The A-type sandwich polyoxometalates of [(HOSnIVOH)3(PW9O34)2]12- (P2W18Sn3) and [(OCeIVO)3(PW9O34)2]12- (P2W18Ce3) were immobilized for the first time into the porous metal-organic framework MIL-101(Cr). FT-IR, powder X-ray diffraction, SEM-EDX, ICP analysis, N2 adsorption and thermogravimetric analysis collectively confirmed immobilization and good distribution of polyoxometalates into cages of MIL-101(Cr). The catalytic activities of the homogeneous P2W18Sn3 and P2W18Ce3 and the corresponding heterogeneous catalysts were examined in the oxidation of sulfides to sulfones with H2O2 as the oxidant at room temperature. The effects of different dosages of polyoxometalates, type of solvent, reaction time, amount of catalyst and oxidant in this catalytic system were investigated. The new P2W18Sn3@MIL-101 and P2W18Ce3@MIL-101 nanocomposites exhibited good recyclability and reusability in at least five consecutive reaction cycles without significant loss of activity or selectivity.
Naseri, Elham,Khoshnavazi, Roushan
p. 28249 - 28260
(2018/08/16)

Oxidoperoxidomolybdenum(VI) complexes with acylpyrazolonate ligands: Synthesis, structure and catalytic properties
Oxidoperoxido-molybdenum(vi) complexes containing acylpyrazolonate ligands were obtained by reaction of [Mo(O)(O)2(H2O)n] with the corresponding acylpyrazolone compounds HQR. Complexes Ph4P[Mo(O)(O2)2(QR)] (R = neopentyl, 1; perfluoroethyl, 2; hexyl, 3; phenyl, 4; naphthyl, 5; methyl, 6; cyclohexyl, 7; ethylcyclopentyl, 8) were obtained if the reaction was carried out with one equivalent of HQR in the presence of Ph4PCl. Alternatively, neutral complexes [Mo(O)(O2)(QR)2] (R = neopentyl, 9; hexyl, 10; cyclohexyl, 11) were formed when two equivalents of HQR were used in the reaction. These complexes were isolated in good yields as yellow or yellow-orange crystalline solids and were spectroscopically (IR, 1H, 13C{1H} and 31P{1H} NMR), theoretically (DFT) and structurally characterised (X-ray for 1, 2, 9 and 10). Compounds 1 and 9 were selected to investigate their catalytic behaviour in epoxidation of selected alkenes and oxidation of selected sulphides, while 10 and 11 were tested as catalyst precursors in the deoxygenation of selected epoxide substrates to alkenes, using PPh3 as the oxygen-acceptor. Complexes Ph4P[Mo(O)(O2)2(QR)] were shown to be poor catalyst precursors in oxidation reactions, while the activity of [Mo(O)(O2)(QR)2] species is good in all the studied reactions and comparable to related oxidoperoxido-molybdenum(vi) complexes. Complex [Mo(O)2(QC6)2], 12, was obtained by treatment of 10 with one equivalent of PPh3, demonstrating that the first step in the epoxide deoxygenation mechanism was the oxygen atom transfer toward the phosphane.
Begines, Emilio,Carrasco, Carlos J.,Montilla, Francisco,álvarez, Eleuterio,Marchetti, Fabio,Pettinari, Riccardo,Pettinari, Claudio,Galindo, Agustín
p. 197 - 208
(2017/12/27)

Aluminum(III) Chloride Promoted Oxygen Transfer: Selective Oxidation of Sulfides to Sulfoxides
An efficient selective oxidation of sulfides to sulfoxides has been developed by means of AlCl 3 -promoted oxygen transfer from phenyliodine diacetate [PhI(OAc) 2 ]. AlCl 3 proved to be the optimalLewis acid for the activation of PhI(OAc) 2. Various substituted sulfides were selectively transformed into the corresponding sulfoxides in good to excellent yields (≤99%). The high efficiency, excellent functional-group compatibility, broad substrate scope, and mild conditions render the current transformation useful for the synthesis of sulfoxides.
Xie, Yongtao,Li, Yuxin,Zhou, Sha,Zhou, Shaa,Zhang, Yan,Chen, Minggui,Li, Zhengming
supporting information
p. 340 - 343
(2017/12/06)

Zeolite nanoparticles (H-ZSM5) as a highly efficient, green, and reusable heterogeneous catalyst for selective oxidation of sulfides to sulfoxides under mild conditions
H-ZSM5 is applied as an efficient, highly reusable, and heterogeneous catalyst for the oxidation of sulfides to sulfoxides using 30% H2O2 under solvent-free conditions at room temperature. A variety of aromatic and aliphatic sulfides with different functional groups were successfully oxidized with good to excellent yields in short reaction times. The catalyst can be easily recovered by simple filtration and recycled for several consecutive runs without any significant loss of its catalytic activity.
Rostami, Amin,Saedmocheshi, Noosheen,Shirvandi, Zeinab
p. 835 - 839
(2018/06/20)

Fe3O4/PEG-SO3H as a heterogeneous and magnetically-recyclable nanocatalyst for the oxidation of sulfides to sulfones or sulfoxides
We present below a sulfonated-polyethylene glycol-coated Fe3O4 nanocomposite (Fe3O4/PEG-SO3H) as a greatly effective and ecological nanocatalyst for the selective oxidation of sulfides to sulfoxides or sulfones with brilliant yields under solvent-free conditions by employing 30% hydrogen peroxide as the oxidant. A number of sulfides containing alcohol, ester, and aldehyde functional groups were fruitfully and selectively oxidized without altering the desired characteristics. The magnetic nanocatalyst (Fe3O4/PEG-SO3H) can be conveniently and swiftly retrieved through the utilization of an external magnetic tool and recycled for more than 10 reaction runs without significantly decreasing its catalytic behavior.
Mirfakhraei, Saeideh,Hekmati, Malak,Eshbala, Fereshteh Hosseini,Veisi, Hojat
p. 1757 - 1761
(2018/02/09)

Synthesis and characterization of oxo-vanadium complex anchored onto SBA-15 as a green, novel and reusable nanocatalyst for the oxidation of sulfides and oxidative coupling of thiols
Abstract: The present work describes the synthesis of a new oxo-vanadium complex immobilized on SBA-15 nanostructure as an efficient catalyst for oxidation of sulfides and oxidative coupling of thiols. Characterization of the resultant AMPD@SBA-15 nanostructure was performed by various physico-chemical techniques such as Fourier transform infrared spectroscopy, transmission and scanning electron microscopies, energy-dispersive X-ray spectroscopy, inductively coupled plasma optical emission spectroscopy, X-ray diffraction, thermal gravimetric analysis, and N2 adsorption and desorption. The results of the developed procedure bring several benefits such as the use of commercially available, ecologically benign, operational simplicity, and cheap and chemically inert reagents. It shows good reaction times, practicability and high efficiency, and is easily recovered from the reaction mixture by simple filtration and reused for several consecutive cycles without noticeable change in its catalytic activity. More importantly, high efficiency, simple and an inexpensive procedure, commercially available materials, easy separation, and an eco-friendly procedure are the several advantages of the currently employed heterogeneous catalytic system.
Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash,Molaei, Somayeh
p. 4259 - 4276
(2018/03/21)

Applications of iron and nickel immobilized on hydroxyapatite-core-shell γ-Fe2O3 as a nanomagnetic catalyst for the chemoselective oxidation of sulfides to sulfoxides under solvent-free conditions
In the present study, Fe2+ and Ni2+ immobilized on hydroxyapatite-core-shell γ-Fe2O3 (γ-Fe2O3@HAp-Fe2+ and γ-Fe2O3@HAp-Ni2+) with a high surface area has been synthesized and characterized by Fourier transform infrared (FTIR), X-ray diffraction (XRD), vibrating sample magnetometer (VSM), transmission electron microscopy (TEM), and scanning electron microscope (SEM) techniques. Then, γ-Fe2O3@HAp-Fe2+ and γ-Fe2O3@HAp-Ni2+ were used as a new and magnetically recoverable nano catalyst for the selective oxidation of sulfides to sulfoxides with 33% aqueous H2O2 (0.5 mL) as an oxidant at room temperature in good to excellent yields and short reaction time. Nontoxicity of reagent, mild reaction condition, inexpensive and high catalytic activity, simple experimental procedure, short period of conversion and excellent yields, and ease of recovery from the reaction mixture using an external magnet are the advantages of the present method.
Sajjadifar, Sami,Rezayati, Sobhan,Arzehgar, Zeinab,Abbaspour, Sima,Torabi Jafroudi, Mogharab
p. 960 - 969
(2018/03/29)

Novel diphenylsulfimide antioxidants containing 2,6-di-tert-butylphenol moieties
New diphenylsulfimide derivatives containing substituents with the 2,6-di-tert-butylphenol moiety at the nitrogen atom were synthesized. Their molecular structures were established by X-ray diffraction. Antioxidant activity was experimentally evaluated by spectrophotometry based on hydrogen transfer to the stable radicals, namely, 2,2-diphenyl-1-picrylhydrazyl and the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS·+), and using in vitro lipid peroxidation in rat brain and liver homogenates. The presence of phenol and diphenylsulfimide moieties in one molecule leads to a significant enhancement of antioxidant activity. The new compounds exhibit moderate inhibitory activity against enzymes involved in carbohydrate and lipid metabolism. The evaluation of antiglycation activity showed that the new sulfimides taken at a concentration of 100 μmol L–1 have activity comparable with that of aminoguanidine.
Milaeva,Shpakovsky,Maklakova,Rufanov,Neganova,Shevtsova,Churakov,Babkova,Babkov,Kosolapov,Spasov
p. 2025 - 2034
(2019/01/08)

Transition-Metal-Free Arylations of In-Situ Generated Sulfenates with Diaryliodonium Salts
A transition-metal-free arylation of sulfenate anions generated from β-sulfinyl esters with diaryliodonium salts was developed. In this process, a new C-S bond is formed under mild reaction conditions providing a wide range of S,S-diaryl and S-alkyl S-aryl sulfoxides.
Yu, Hao,Li, Zhen,Bolm, Carsten
supporting information
p. 7104 - 7106
(2018/11/23)

Visible-Light-Driven Silver-Catalyzed One-Pot Approach: A Selective Synthesis of Diaryl Sulfoxides and Diaryl Sulfones
An efficient one-pot approach for the synthesis of diaryl sulfoxides and diaryl sulfones using aryl thiols and aryl diazonium salts was developed. The use of a visible-light-driven silver catalysis and the subsequent singlet-oxygen-induced oxidation enabled selective synthesis of sulfoxides and sulfones in the absence of a photocatalyst. The reactions were carried out under mild reaction conditions; the desired products were obtained under air atmosphere at room temperature.
Kim, Dong Hyuk,Lee, Juyoung,Lee, Anna
supporting information
p. 764 - 767
(2018/02/09)

One-pot synthesis of α-phenylsulfinyl ketones by reaction of phenyl benzenethiosulfinate with enolate anions, and synthesis of sulfoxides and sulfides by its reaction with Grignard reagents
Phenyl benzenethiosulfinate reacts with enolate anions derived from ketones to give α-phenylsulfinyl ketones directly, together with minor amounts of α-phenylsulfanyl ketones. These are easily separated by forming the water-soluble sodium salts of the sulfinyl compounds. Grignard reagents also react with phenyl benzenethiosulfinate, to give mixtures of sulfoxides and sulfides.
Fakhry, Jerome,Grayson, David H.
p. 556 - 563
(2017/12/28)

Enantioselective Synthesis of Chiral-at-Sulfur 1,2-Benzothiazines by CpxRhIII-Catalyzed C?H Functionalization of Sulfoximines
Sulfoximines with stereogenic sulfur atoms are attractive structural motifs in drug discovery. A direct catalytic enantioselective method for the synthesis of sulfur-chiral 1,2-benzothiazines from readily accessible diaryl sulfoximines is presented. Rhodium(III) complexes equipped with chiral cyclopentadienyl ligands and paired with suitable carboxylic acid additives engage in an enantiodetermining C?H activation directed by the sulfoximine group. Subsequent trapping of the rhodacycle with a broad range of diazoketones gives access to S-chiral 1,2-benzothiazines with synthetically highly attractive substitution patterns in good yields and enantioselectivities.
Sun, Yang,Cramer, Nicolai
supporting information
p. 15539 - 15543
(2018/11/02)

Synthesis and characterization of PMoV/Fe3O4/g-C3N4 from melamine: An industrial green nanocatalyst for deep oxidative desulfurization
A facile approach to the preparation of a novel magnetically separable H5PMo10V2O40/Fe3O4/g-C3N4 (PMoV/Fe3O4/g-C3N4) nanocomposite by chemical impregnation is demonstrated. The prepared nanocomposite was characterized and its acidity was measured by potentiometric titration. PMoV/Fe3O4/g-C3N4 showed high catalytic activity in the selective oxidative desulfurization of sulfides to their corresponding sulfoxides or sulfones. The catalytic oxidation of a dibenzothiophene (DBT)-containing model oil and that of real oil were also studied under optimized conditions. In addition, the effects of various nitrogen compounds, as well as the use of one- and two-ring aromatic hydrocarbons as co-solvents, on the catalytic removal of sulfur from DBT were investigated. The catalyst was easily separated and could be recovered from the reaction mixture by using an external magnetic field. Additionally, the remaining reactants could be separated from the products by simple decantation if an appropriate solvent was chosen for the extraction. The advantages of this nanocatalyst are its high catalytic activity and reusability; it can be used at least four times without considerable loss of activity.
Rafiee, Ezzat,Khodayari, Maryam
p. 458 - 468
(2017/04/04)

A Simple Metal Free Oxidation of Sulfide Compounds
Abstract: This work reports simple, efficient, selective protocol for the oxidation of sulfide compounds. Various sulfides were selectively and completely converted into their corresponding sulfoxides and sulfones using H2O2as an oxidant in presence of catalytic amount of caprylic acid. The reaction proceeds at room temperature to give sulfoxide and by increasing the reaction temperature to 50 °C, this system provides selective formation of sulfone with high conversion and excellent yields. Green, convenient, easy work-up, chemoselectivity, broad substrate scope and regeneration of catalyst are the important highlights of this protocol. Graphical Abstract: [Figure not available: see fulltext.] Using H2O2as an oxidant in presence of catalytic amount of caprylic acid various sulfides were selectively and completely converted into their corresponding sulfoxides and sulfones.
Wagh, Ravindra B.,Nagarkar, Jayashree M.
p. 181 - 187
(2017/02/18)

A Mild, Efficient and Highly Selective Oxidation of Sulfides to Sulfoxides Catalyzed by Lewis Acid–Urea–Hydrogen Peroxide Complex at Room Temperature
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
p. 2173 - 2177
(2017/07/25)

Exploiting a beast in carbenoid chemistry: Development of a straightforward direct nucleophilic fluoromethylation strategy
The first direct and straightforward nucleophilic fluoromethylation of organic compounds is reported. The tactic employs a fleeting lithium fluorocarbenoid (LiCH2F) generated from commercially available fluoroiodomethane. Precise reaction conditions were developed for the generation and synthetic exploitation of such a labile species. The versatility of the strategy is showcased in ca. 50 examples involving a plethora of electrophiles. Highly valuable chemicals such as fluoroalcohols, fluoroamines, and fluoromethylated oxygenated heterocycles could be prepared in very good yields through a single synthetic operation. The scalability of the reaction and its application to complex molecular architectures (e.g., steroids) are documented.
Parisi, Giovanna,Colella, Marco,Monticelli, Serena,Romanazzi, Giuseppe,Holzer, Wolfgang,Langer, Thierry,Degennaro, Leonardo,Pace, Vittorio,Luisi, Renzo
supporting information
p. 13648 - 13651
(2017/11/06)

Anchoring of Cu(II)–vanillin Schiff base complex on MCM-41: A highly efficient and recyclable catalyst for synthesis of sulfides and 5-substituted 1H–tetrazoles and oxidation of sulfides to sulfoxides
A copper(II)–vanillin complex was immobilized onto MCM-41 nanostructure and was used as an inexpensive, non-toxic and heterogeneous catalyst in the synthesis of symmetric aryl sulfides by the cross-coupling of aromatic halides with S8 as an effective sulfur source, in the oxidation of sulfides to sulfoxides using 30% H2O2 as a green oxidant and in the synthesis of 5-substituted 1H–tetrazoles from a smooth (3?+?2) cycloaddition of organic nitriles with sodium azide (NaN3). The products were obtained in good to excellent yields. This catalyst could be reused several times without loss of activity. Characterization of the catalyst was performed using Fourier transform infrared, energy-dispersive X-ray and atomic absorption spectroscopies, X-ray diffraction, thermogravimetric analysis, and scanning and transmission electron microscopies.
Khanmoradi, Maryam,Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash
(2017/09/01)

Direct Irradiaton of Aryl Sulfides: Homolytic Fragmentation and Sensitized S-Oxidation
The direct irradiation of diphenyl sulfide and p-substituted thioanisoles in the presence of oxygen was investigated by means of both steady state and laser flash photolysis experiments. Two competitive pathways took place from the triplet excited state o
Bonesi, Sergio M.,Crespi, Stefano,Merli, Daniele,Manet, Ilse,Albini, Angelo
p. 9054 - 9065
(2017/09/11)

In situ generation of highly active bis(N-heterocyclic)carbene palladium as an efficient catalyst in direct S-arylation of methylphenyl sulfoxide and the Heck reaction: Ligand steric effects in product selectivity
The use of 1,3-bis(N-heterocyclic)carbene ligands with different alkyl wingtip groups (alkyl = methyl, isopropyl and tert-butyl) is an effective method for the palladium-catalysed direct S-arylation of methylphenyl sulfoxide and C–C coupling of various of aryl halides with alkenes. The reactions proceed in moderate to good yields. Interestingly, it is shown experimentally that, by using bulkier bidentate N-heterocyclic carbene ligands, more selective catalytic systems towards cis products in Heck coupling reactions can be achieved.
Bagherzadeh, Mojtaba,Mousavi, Narges-Alsadat,Jamali, Sirous
(2017/07/25)

Nano-sized mesoporous sodium iron hydroxyphosphate supported gold: An effective catalyst for the oxidation of sulfides
New nano-sized mesoporous sodium iron hydroxyphosphate (SIHP, Na4.55Fe(PO4)2H0.45O), synthesized by a microemulsion-hydrothermal synthesis method, with supported gold nanoparticles (AuNPs) could be a very effective catalyst for the selective oxidation of sulfides. The results showed that the SIHP material was an excellent catalyst support due to its special structure and the interactions between the AuNPs and the surface hydroxyl groups.
Liu, Junhua,Liu, Gui,Liu, Cheng,Li, Wenxiu,Wang, Fang
p. 2055 - 2059
(2016/04/26)

An eco-friendly oxidation of sulfide compounds
An improved green route has been developed for the oxidation of sulfide compounds. Albendazole is converted to ricobendazole or albendazole sulfone using H 2O2 as an oxidant and H 2O as the solvent. High yields of the corresponding products were obtained by carrying out the reaction at room temperature. This synthetic method is environmentally clean and safe, operationally simple for the oxidation of other benzimidazole anthelmintics and various sulfide compounds. [Figure not available: see fulltext.]
Wagh, Ravindra B,Gund, Sitaram H,Nagarkar, Jayashree M
p. 1321 - 1325
(2016/08/19)

Application of sodium titanate nanotubes doped with vanadium (VNaTNT) as a heterogeneous catalyst for oxidation of sulfides at room temperature
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
p. 494 - 501
(2016/04/20)

Dirhodium(II)-Catalyzed Sulfide Oxygenations: Catalyst Removal by Coprecipitation with Sulfoxides
The dirhodium(II) carboxylate complex Rh2(esp)2 (esp = α,α,α′,α′-tetramethyl-1,3-benzenedipropanoate) was shown to catalyze the sulfoxidation of organic sulfides using tert-butyl hydroperoxide as the oxidant. Due to the unique structure of Rh2(esp)2 and its stable Rh2(II,II) catalyst resting state, the rhodium catalyst is able to precipitate as a Rh2(esp)2-sulfoxide complex following the reaction which makes separation of the catalyst from the products very convenient. The precipitated Rh2(esp)2-sulfoxide complexes could be reused to catalyze sulfide oxygenation reactions without considerable loss of activity. Mechanistic studies suggest that the axial ligands fine-tune the redox potential of the dirhodium(II,II) compounds and determine the predominant catalyst species in the oxidation reaction.
Zhao, Lili,Zhang, Hongyang,Wang, Yuanhua
p. 129 - 136
(2016/01/15)

Magnetically separable chicken feathers: A biopolymer based heterogeneous catalyst for the oxidation of organic substrates
Magnetically separable poultry chicken feathers were found to be an efficient, green and heterogeneous catalyst for the oxidation of alcohols and sulfides to the corresponding carbonyl compounds and sulfoxides, respectively using t-butyl hydroperoxide (TBHP) as oxidant with complete selectivity and high conversions. The developed catalyst exhibited higher stability, activity and better recycling ability than the bare magnetic nanoparticles. The designed catalyst could readily be recovered using an external magnet without showing any significant leaching during the reaction.
Patnam, Padma L.,Bhatt, Mukesh,Singh, Raghuvir,Saran, Sandeep,Jain, Suman L.
p. 60888 - 60895
(2016/07/11)

Peroxomolybdate supported on water soluble polymers as efficient catalysts for green and selective sulfoxidation in aqueous medium
Peroxomolybdenum(VI) species immobilized on linear water soluble polymers formulated as, [MoO(O2)2(sulfonate)]–PS [PS?=?poly(sodium vinyl sulfonate)] (PSMo) and[Mo2O2(O2)4(carboxylate)]–PA [PA?=?poly(sodium acrylate)](PAMo) served as efficient and recyclable catalysts for selective oxidation of organic sulfides to sulfoxide in water with 30% H2O2. The new polymer anchored complex, PSMo has been prepared by reacting H2MoO4 and 30% H2O2 with macromolecular ligand, poly(sodium vinyl sulfonate) and characterized by elemental analysis, spectral studies (FTIR, Raman, 13C NMR, 95Mo NMR, UV–vis), SEM, EDX and TGA-DTG analysis. The catalytic protocol effects clean and facile oxidation of a wide range of sulfides to afford pure sulfoxides with high TOF and excellent chemoselectivity at ambient temperature,with an easy work-up procedure. The catalysts can be regenerated in-situ and recycled at least up to ten consecutive reaction cycles without significant loss of activity and are amenable for ready scalability. The catalytic procedure thus provides an ecologically sustainable alternative as it involves water as solvent, H2O2 as green oxidant, a recyclable non-polluting catalyst, and is absolutely free from halide, organic co-solvent or co-catalyst. This is the first catalytic protocol for selective aqueous oxidation of sulfides using a catalytic system based on peroxometal species supported on water soluble polymers.
Boruah, Jeena Jyoti,Ahmed, Kabirun,Das, Srewashi,Gogoi, Sandhya Rani,Saikia, Gangutri,Sharma, Mitu,Islam, Nashreen S.
p. 21 - 30
(2016/09/28)

By means of a micro channel reactor method of preparing sulfoxide or sulfone
The invention discloses a method for preparing sulfoxide or sulfone by using a micro-channel reactor. The invention provides a method for preparing sulfoxide or sulfone. The method comprises the following steps: respectively feeding a homogeneous solution prepared from thioether 1 and a solvent, and an oxidant into the micro-channel reactor, and contacting the homogeneous solution with the oxidant in a micro-channel for oxidation reaction so as to obtain sulfoxide or sulfone, wherein the oxidation reaction time is 1-300 seconds. The method disclosed by the invention is very short in reaction time, precise in reaction condition control, high in security, applicable to rapid preparation of kilogram-scale products and capable of realizing continuous production; the sulfoxide and sulfone are high in selectivity, high in yield, good in purity and applicable to on-scale industrial production.
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Paragraph 0055-0059

(2017/04/11)

A simple one-pot and transition metal-free synthesis of diaryl- and dialkyl sulfides via grignard reaction/deoxygenation
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Jung, Hee Seon,Suh, Nuri,Jeon, Heung Bae
p. 779 - 782
(2016/05/19)

Aminoxidation of Arenethiols to N-Chloro-N-sulfonyl Sulfinamides
A simple and efficient method to synthesize N-chloro-N-sulfonylsulfinamides by the direct aminoxidation of arenethiols under aqueous and mild conditions is disclosed, geminally installing the oxo and amino groups on the sulfur atom of arenethiols. The products have been primarily developed as sulfinylation reagents to convert Grignard reagents into sulfoxides, and as amination reagents to convert secondary amines into hydrazine derivatives.
Yang, Zhanhui,Xu, Wei,Wu, Qiuyue,Xu, Jiaxi
p. 3051 - 3057
(2016/04/26)

Palladium-Catalyzed Arylation of Aryl Sulfenate Anions with Aryl Bromides under Mild Conditions: Synthesis of Diaryl Sulfoxides
A palladium-catalyzed arylation of aryl sulfenate anions generated from aryl 2-(trimethylsilyl)ethyl sulfoxides and CsF has been developed. This protocol is effective for the synthesis of diaryl sulfoxides and heteroaryl aryl sulfoxides under mild conditions employing aryl bromides. Various functional groups, including those with acidic protons, are well tolerated.
Jiang, Hui,Jia, Tiezheng,Zhang, Mengnan,Walsh, Patrick J.
supporting information
p. 972 - 975
(2016/03/15)

Selective Synthesis of Sulfoxides through Oxidation of Sulfides with Sodium Hypochlorite Pentahydrate Crystals
Oxidation of sulfides with sodium hypochlorite pentahydrate crystals (1.1 equiv) in an aqueous acetonitrile solution selectively produces the corresponding sulfoxides in high yields. This procedure is catalyst-free and environmentally benign.
Okada, Tomohide,Matsumuro, Hiroaki,Kitagawa, Saori,Iwai, Toshiaki,Yamazaki, Kento,Kinoshita, Yukari,Kimura, Yoshikazu,Kirihara, Masayuki
p. 2547 - 2552
(2015/11/16)