- Molybdenum (VI)-functionalized UiO-66 provides an efficient heterogeneous nanocatalyst in oxidation reactions
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A novel heterogeneous nanocatalyst was established by supporting molybdenum (VI) on Zr6 nodes in the structure of the well-known UiO-66 metal–organic framework (MOF). The structure of the UiO-66 before and after Mo (VI) immobilization was confirmed with XRD, DR-FTIR and UV–vis spectroscopy, and the presence and amount of Mo (VI) was identified by X-ray photoelectron spectroscopy and inductively coupled plasma atomic emission spectroscopy. TEM imaging confirmed the absence of Mo clusters on the MOF surface, while SEM confirmed that the appearance of the MOF has not changed upon immobilizing the Mo (VI) catalyst. BET adsorption measurements were used to confirm the porosity of the catalyst. The catalytic activity of this heterogeneous catalyst was investigated in oxidation of sulfides with H2O2 in acetonitrile and oxidative desulfurization of dibenzothiophene. Easy work up, convenient and steady reuse and high activity and selectivity are prominent properties of this new hybrid material.
- Afzali, Niloufar,Kardanpour, Reihaneh,Zadehahmadi, Farnaz,Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah,Mechler, Adam,Mohammadpoor-Baltork, Iraj,Bahadori, Mehrnaz
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Read Online
- On the important transition of sugar-based surfactant as a microreactor for C-S coupling in water: From micelle to vesicle
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A reversible, temperature-induced micelle-to-vesicle transition of a sugar-based pseudogemini surfactant (C11D12) was employed for copper-catalyzed C-S coupling in water. The phase behavior and morphology of the C11D12 aqueous solution were investigated by DLS and cryo-TEM. The aggregates undergo a series of transitions upon increasing the temperature: spherical micelles were initially transformed into large vesicles, but they eventually transformed into smaller vesicles. The vesicular catalytic protocol accommodates an excellent substrate scope with moderate to high yields. The mechanisms of temperature-induced aggregate transition and vesicular catalysis were elucidated by experimental results and DFT calculations. It was revealed that the charge layer of the vesicle grants stronger nucleophilicity to the PhSO2-Cu-D12Ga intermediate. Furthermore, the aqueous reaction medium can be recycled and reused several times after easily separating the precipitated product.
- Ge, Xin,Lei, Qiuyun,Liao, Xiong,Liu, Xuemin,Song, Weili,Wu, Lei,Wu, Siyuan,Zhou, Shaodong
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- Synthesis, spectral characterization, SC-XRD, HSA, DFT and catalytic activity of novel dioxovanadium(V) complex with aminobenzohydrazone Schiff base ligand: An experimental and theoretical approach
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A new dioxovanadium(V) complex was prepared by the reaction of VO(acac)2 with a tridentate ONO donor Schiff base, derived by condensing 3-ethoxysalicylaldehyde and 4-aminobenzohydrazide. The structures of synthesized products were characterized spectroscopically through FT-IR, 1H & 13C NMR and by elemental composition through combustion analysis. The structure of the complex was determined with the help of single crystal X-ray crystallography. It was inferred from the diffraction data that the geometry around the central metal ion in the complex is distorted square pyramidal. The tridentate Schiff base ligand is bonded to the central metal through the oxygen of the carbonyl group, the deprotonated phenolic oxygen atom and the azomethine nitrogen. The pyramid base is completed by other oxo ligands that are in cis positions. The theoretical calculations, performed by DFT using B3LYP/Def2-TZVP level of theory, determined that the intended outcomes are in compliance with the actual consequences. Furthermore, the catalytic potential of the vanadium complex was explored for the selective oxidation of the aryl and alkyl sulfides to the corresponding sulfones in the presence of 30% aqueous H2O2 in ethanol. In this work, rPBE and B3LYP methods are used to locate transition structures and to compare free energies of reactants, transition structures and the products involved in the reaction. Analyzing nudge elastic band data shows that the barrier free energy for the oxidation of sulfide to sulfoxide and sulfone are 13 and 83 kcal.mol?1, respectively. The main advantages of the present catalytic study are high yields of the products, less time required for the completion of the reaction and simple work-out procedure.
- Ashfaq, Muhammad,Behjatmanesh-Ardakani, Reza,Fallah-Mehrjardi, Mehdi,Kargar, Hadi,Munawar, Khurram Shahzad,Tahir, Muhammad Nawaz
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- Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide
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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
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supporting information
p. 8691 - 8695
(2021/10/22)
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- Synthesis, spectra (FT-IR, NMR) investigations, DFT, FMO, MEP, NBO analysis and catalytic activity of MoO2(VI) complex with ONO tridentate hydrazone Schiff base ligand
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A new dioxomolybdenum(VI) complex has been successfully prepared by the reaction of an ONO donor Schiff base, derived by condensing 4-amino-2-hydroxybenzohydrazide and 3-ethoxysalicylaldehyde, with MoO2(acac)2. The structures of synthesized products were explored spectroscopically through FT-IR, 1H & 13C NMR and by elemental composition (CHN) through combustion analysis. The tridentate Schiff base ligand is bonded to the central metal through its deprotonated enolic and phenolic oxygen atoms and by the nitrogen of the azomethine group. The interpretation of the data obtained through diffraction analysis validates the distorted octahedral geometry for the prepared metal complex. Furthermore, the catalytic potential of the molybdenum complex was explored for the selective oxidation of the aryl and alkyl sulfides to the corresponding sulfones in the presence of 30% aqueous H2O2 in ethanol. The main edge of the present catalytic work is the accomplishment of reaction in a short period of time, high percentage yield and easy work-up procedure.
- Behjatmanesh-Ardakani, Reza,Fallah-Mehrjardi, Mehdi,Kargar, Hadi,Munawar, Khurram Shahzad
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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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- COMPOSITES, METHODS AND USES THEREOF
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The present invention relates, in general terms, to methods of catalysing a reaction, including the steps of contacting a chemical entity comprising a sulphide moiety with a composite and an oxidant. The composite acts as a heterogeneous catalyst to oxidise the sulphide moiety. The present invention also relates to composites, methods of synthesising the composites and its use as a catalyst thereof.
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Page/Page column 26
(2021/06/04)
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- Ceramic boron carbonitrides for unlocking organic halides with visible light
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Photochemistry provides a sustainable pathway for organic transformations by inducing radical intermediates from substrates through electron transfer process. However, progress is limited by heterogeneous photocatalysts that are required to be efficient, stable, and inexpensive for long-term operation with easy recyclability and product separation. Here, we report that boron carbonitride (BCN) ceramics are such a system and can reduce organic halides, including (het)aryl and alkyl halides, with visible light irradiation. Cross-coupling of halides to afford new C-H, C-C, and C-S bonds can proceed at ambient reaction conditions. Hydrogen, (het)aryl, and sulfonyl groups were introduced into the arenes and heteroarenes at the designed positions by means of mesolytic C-X (carbon-halogen) bond cleavage in the absence of any metal-based catalysts or ligands. BCN can be used not only for half reactions, like reduction reactions with a sacrificial agent, but also redox reactions through oxidative and reductive interfacial electron transfer. The BCN photocatalyst shows tolerance to different substituents and conserved activity after five recycles. The apparent metal-free system opens new opportunities for a wide range of organic catalysts using light energy and sustainable materials, which are metal-free, inexpensive and stable. This journal is
- Yuan, Tao,Zheng, Meifang,Antonietti, Markus,Wang, Xinchen
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p. 6323 - 6332
(2021/05/19)
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- Synthesis of sulfone derivatives via palladium-catalyzed cross-coupling of benzyl trimethylammonium triflates and sulfonyl hydrazides
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A palladium-catalyzed cross-coupling of benzyl trimethylammonium triflates and sulfonyl hydrazides for the synthesis of various benzyl sulfones is reported. This novel protocol shows widespread functional group tolerance, leading to the desired sulfones in moderate to excellent yields.
- Luo, Jin,Wan, Juelin,Wang, Tao,Yu, Weijie
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supporting information
(2021/12/31)
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- Interfacing sugar-based surfactant micelles and Cu nanoparticles: A nanoreactor for C-S coupling reactions in water
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A simple and sustainable synergistic catalytic protocol by interfacing nanomicelles and metal nanoparticles (MNPs) is reported for C-S coupling reactions in water. The sugar-based surfactant GluM was synthesized by introducing a PEG chain to stabilize MNPs and self-assembled to form nanomicelles. Cu2O nanoparticles were generated via in situ reduction of copper salt in an aqueous solution of the sugar-based surfactant. The nature of the interaction between nanomicelles and Cu2O nanoparticles was revealed by XPS, XRD, in situ IR, TEM, and 1H NMR. A broad substrate scope with moderate to excellent yields was documented and the recycling of the GluM/Cu aqueous mixture was surprising.
- Ge, Xin,He, Xi,Liu, Xuemin,Qian, Chao,Song, Weili,Yang, Jinguo,Zhou, Shaodong
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supporting information
p. 6322 - 6329
(2021/09/10)
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- Desulfonylative Electrocarboxylation with Carbon Dioxide
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Electrocarboxylation of organic halides is one of the most investigated electrochemical approaches for converting thermodynamically inert carbon dioxide (CO2) into value-added carboxylic acids. By converting organic halides into their sulfone derivatives, we have developed a highly efficient electrochemical desulfonylative carboxylation protocol. Such a strategy takes advantage of CO2as the abundant C1 building block for the facile preparation of multifunctionalized carboxylic acids, including the nonsteroidal anti-inflammatory drug ibuprofen, under mild reaction conditions.
- Zhong, Jun-Song,Yang, Zi-Xin,Ding, Cheng-Lin,Huang, Ya-Feng,Zhao, Yi,Yan, Hong,Ye, Ke-Yin
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p. 16162 - 16170
(2021/09/02)
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- Synthesis of Sulfones and Sulfonyl Derivatives using Sodium (tert-butyldimethylsilyl)oxymethanesulfinate
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The present invention relates to a method for manufacturing a sulfone and sulfonyl derivative compound using sodium (tert-butyldimethylsilyl)oxymethanesulfinate, which is a novel organic sulfin salt, wherein the novel organic sulfin salt has good stability, environmental friendliness and economy, and is easy to handle, and thus significantly reduces the amount of transition metal catalysts and the amount of organic sulfin salts used when introducing aryl or alkenyl. Also, alkylation, arylation, amination, and fluorination are all possible during secondary functionalization. Therefore, the present invention can be usefully used in preparation and mass production of various kinds of sulfones and derivatives thereof including asymmetric sulfone derivatives.
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Paragraph 0836-0841; 0843; 0845-0846; 0848-0851; 0858-0861
(2021/04/29)
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- One-pot synthesis of sulfones via Ni(II)-catalyzed sulfonylation of boronic acids, Na2S2O5 and benzylic ammonium salts
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A one-pot nickel-catalyzed synthesis of (hetero)aryl alkyl sulfones from readily available boronic acids, sodium metabisulfite and benzylic ammonium salts as electrophiles is described. This general and efficient synthetic process is of broad scope, occurs in two steps, and delivers structural diverse sulfones, and the intermediate sulfinate is isolated. The transformation exhibits application of benzylic ammonium salts as novel electrophiles for direct insertion of SO2 as a novel area to be investigated.
- Zhu, Haibo,Liu, Yishuai,Zhang, Yingying,Yang, Liu,Meng, Jia,Li, Qian,Gong, Bozhen,Xie, Zongbo,Le, Zhang-Gao
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- Cobalt-Catalyzed Redox-Neutral Sulfonylative Coupling from (Hetero)aryl Boronic Acids, Ammonium Salts and Potassium Metabisulfite
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An efficient cobalt-catalyzed redox-neutral sulfonylative coupling to afford (hetero)aryl alkyl sulfones from boronic acids, ammonium salts and potassium metabisulfite has been realized. Commercially available and air-stable CoCl2, in combination with phenanthroline ligand, is sufficient to achieve rapid and high-yielding conversion of the reactants into the corresponding sulfones. This practical transformation proceeds smoothly through C?N bond cleavage under redox-neutral catalytic conditions and shows broad functional-group tolerance. Other carbon based electrophiles, including diaryliodonium salts, heteroaryl halides, and carbonates were compatible. Further transformation of aryl alkyl sulfones then allows conversion into olefins, alkenyl sulfones and halogenated sulfones, respectively, in a one-pot process.
- Fan, Qiangwen,Le, Zhang-Gao,Xie, Zongbo,Yang, Liu,Zhang, Yingying,Zhu, Haibo
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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
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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.
- Behjatmanesh-Ardakani, Reza,Fallah-Mehrjardi, Mehdi,Kargar, Hadi,Moghimi, Atefeh,Munawar, Khurram Shahzad,Rudbari, Hadi Amiri
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- Continuous bioinspired oxidation of sulfides
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A simple, efficient, and selective oxidation under flow conditions of sulfides into their corresponding sulfoxides and sulfones is reported herein, using as a catalyst perselenic acid generated in situ by the oxidation of selenium (IV) oxide in a diluted aqueous solution of hydrogen peroxide as the final oxidant. The scope of the proposed methodology was investigated using aryl alkyl sulfides, aryl vinyl sulfides, and dialkyl sulfides as substrates, evidencing, in general, a good applicability. The scaled-up synthesis of (methylsulfonyl)benzene was also demonstrated, leading to its gram-scale preparation.
- Crociani, Letizia,Mangiavacchi, Francesca,Marini, Francesca,Sancineto, Luca,Santi, Claudio
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- Ag?CeO2 nanoparticles with “rice ball” configuration as an efficient and heterogeneous nanocatalyst for the selective oxidation of sulfides to sulfones with 30% H2O2
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Abstract: Ag?CeO2 with a rice-ball configuration as a heterogeneous and highly efficient catalyst was described for activation of H2O2 in the selective oxidation of aromatic and aliphatic sulfides to their corresponding sulfones. Ag nanoparticles in the CeO2–Ag interface increase the oxygen vacancy defects on the surface of CeO2 and oxygen vacancy defects promote the reduction of Ce4+ to Ce3+ to keep the electroneutrality. Generated Ce3+ species act as the active sites in the interface of CeO2–Ag to promote the oxidation of sulfides to sulfones. Compatibility with various aromatic and aliphatic sulfides, excellent selectivity, high yield of product, simple experimental procedure, and mild reaction conditions are some of the precious advantages of Ag?CeO2/H2O2 catalyst system. Graphic abstract: [Figure not available: see fulltext.]
- Bahrami, Kiumars,Ghorbani, Somayeh,Parnian, Rouhallah,Soleimani, Ebrahim
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- Mo(VI) complex catalysed synthesis of sulfonees and their modification for anti-HIV activities
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An efficient method for the synthesis of sulfones has been developed using sugar derived cis-dioxo molybdenum(VI) complex as catalyst and urea hydrogen peroxide as oxygen source. Present method is highly specific for sulfide oxidation irrespective of presence of alkene and aldehyde groups in the same molecule. Synthesis of fifteen sulfones have been reported with 82–98% isolated yields and the catalyst has been reused five times without any loss in its activity. 2-(Phenylsulfonyl)aniline has been condensed with eight different aromatic aldehydes and the products are being explored for HIV-1 reverse transcriptase inhibition activities.
- Madduluri, Vimal Kumar,Baig, Noorullah,Chander, Subhash,Murugesan, Sankaranarayanan,Sah, Ajay K.
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- Genome Mining of Oxidation Modules in trans-Acyltransferase Polyketide Synthases Reveals a Culturable Source for Lobatamides
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Bacterial trans-acyltransferase polyketide synthases (trans-AT PKSs) are multimodular megaenzymes that biosynthesize many bioactive natural products. They contain a remarkable range of domains and module types that introduce different substituents into growing polyketide chains. As one such modification, we recently reported Baeyer–Villiger-type oxygen insertion into nascent polyketide backbones, thereby generating malonyl thioester intermediates. In this work, genome mining focusing on architecturally diverse oxidation modules in trans-AT PKSs led us to the culturable plant symbiont Gynuella sunshinyii, which harbors two distinct modules in one orphan PKS. The PKS product was revealed to be lobatamide A, a potent cytotoxin previously only known from a marine tunicate. Biochemical studies show that one module generates glycolyl thioester intermediates, while the other is proposed to be involved in oxime formation. The data suggest varied roles of oxygenation modules in the biosynthesis of polyketide scaffolds and support the importance of trans-AT PKSs in the specialized metabolism of symbiotic bacteria.
- Ueoka, Reiko,Meoded, Roy A.,Gran-Scheuch, Alejandro,Bhushan, Agneya,Fraaije, Marco W.,Piel, J?rn
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supporting information
p. 7761 - 7765
(2020/03/25)
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- Base-controlled divergent synthesis of vinyl sulfones from (benzylsulfonyl)benzenes and paraformaldehyde
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A tuneable metal-free protocol for the selective preparation of a-substituted vinyl sulfone and (E)-vinyl sulfone derivatives has been described. In this process, stable paraformaldehyde was used as the carbon source. The base played an important role in the selectivity control of transformations. More than 50 products were synthesized with excellent chemoselectivity and broad functional group tolerance.
- Xiao, Fuhong,Hu, Yangling,Huang, Huawen,Xu, Fen,Deng, Guo-Jun
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supporting information
p. 3527 - 3535
(2020/05/25)
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- Silyloxymethanesulfinate as a sulfoxylate equivalent for the modular synthesis of sulfones and sulfonyl derivatives
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An efficient protocol for the modular synthesis of sulfones and sulfonyl derivatives has been developed utilizing sodium tert-butyldimethylsilyloxymethanesulfinate (TBSOMS-Na) as a sulfoxylate (SO22-) equivalent. TBSOMS-Na, easily prepared from the commercial reagents Rongalite and TBSCl, serves as a potent nucleophile in S-alkylation and Cu-catalyzed S-arylation reactions with alkyl and aryl electrophiles. The sulfone products thus obtained can undergo the second bond formation at the sulfur center with various electrophiles without a separate unmasking step to afford sulfones and sulfonyl derivatives such as sulfonamides and sulfonyl fluorides.
- Kim, Dae-Kwon,Um, Hyun-Suk,Park, Hoyoon,Kim, Seonwoo,Choi, Jin,Lee, Chulbom
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p. 13071 - 13078
(2021/01/09)
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- Method for synthesizing organic sulfone molecules by using novel sulfone benzylation reagent
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The invention belongs to the technical field of organic synthesis, and particularly relates to a method for synthesizing organic sulfone molecules by using a novel sulfone benzylation reagent. Easilyavailable sulfonylhydrazine and dibenzyl phosphite are taken as initial reaction raw materials, N,N-dimethylformamide (DMF) is taken as a reaction medium, sodium iodide (NaI) is taken as a catalyst, and organic sulfone molecules are synthesized through reaction at 60 DEG C, wherein dibenzyl phosphite is a novel sulfone benzylation reagent. The method has the advantages that the raw materials are cheap and easy to obtain, the method can be amplified to gram-level reaction to synthesize the active organic sulfone molecule with the sulfone benzyl structure, complex reaction conditions such as anytransition metal catalyst are not needed in the reaction, and heavy metal residues of the synthesized active drug molecule and pollution to the environment are avoided.
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Paragraph 0008-0009; 0013-0015
(2020/12/31)
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- Cu2O-catalyzed C–S coupling of quaternary ammonium salts and sodium alkane-/arene-sulfinates
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A new protocol for the synthesis of (enantioenriched) benzylic sulfones via the Cu2O-catalyzed C–S bond cross coupling of alkane-/arene-sulfinates and (enantioenriched) benzylic quaternary ammonium salts has been developed. The product benzylic sulfones were obtained in good to high yields (75–96%). Chiral arylmethyl sulfones with high enantiomeric excess (90–94% ee) were also synthesized in the presence of Cu2O and 1,1′-bis-(diphenylphosphino)ferrocene (dppf).
- Chen, Hongyi,Huang, Youming,Zeng, Qingle,Zheng, Wenting
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- Cyanide-Mediated Synthesis of Sulfones and Sulfonamides from Vinyl Sulfones
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We report a facile synthesis of sulfones, β-keto sulfones, and sulfonamides from vinyl sulfones via an addition-elimination sequence where in situ generation of nucleophilic sulfinate ion is mediated by cyanide. The use vinyl sulfones renders high selectivity for S -alkylation to produce sulfones in high yields. In the presence of N -bromosuccinimide, primary and secondary amines underwent sulfonamide formation. A preliminary mechanistic study showed the formation of acrylonitrile as an innocent byproduct, without interfering with the desired reaction pathway while generating a sulfinate nucleophile.
- Lee, Ji-Woong,Roy, Tamal
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p. 455 - 458
(2020/03/13)
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- Syntheses of diarylethenes by perylene-catalyzed photodesulfonylation from ethenyl sulfones
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Diarylethenes were obtained from the corresponding ethenyl sulfones by photocatalyzed desulfonylation using UV or blue LEDs. When perylene and i-Pr2NEt were used as a photocatalyst and a sacrificing reagent, respectively, this desulfonylation proceeded smoothly to afford the desired ethenes with the functional groups such as chloro, alkoxy and heteroaromatic rings remaining untouched. The use of a flow photoreactor enabled this desulfonylation to proceed more rapidly to finish in an hour of residence time.
- Adachi, Kazumasa,Dakegata, Aki,Fukuyama, Takahide,Okuda, Yasuhiro,Orita, Akihiro,Ryu, Ilhyong,Takemoto, Mai,Wakamatsu, Kan,Watanabe, Hikaru
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supporting information
p. 409 - 412
(2020/04/27)
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- Multicomponent Synthesis of Sulfones and Sulfides from Triarylbismuthines and Sodium Metabisulfite in Deep Eutectic Solvents
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This study describes a novel and catalyst-free methodology for the multicomponent synthesis of a broad range of sulfones, disulfides, and sulfides from non-toxic triarylbismuthines (Ar3Bi) and sodium metabisulfite (Na2S2O5) in deep eutectic solvents (DESs). The fine tuning of the DESs properties allowed the solubility of all reagents, enhancing their reactivity, as well as, the recyclability of the reaction medium for at least 5 consecutive cycles. Thus, this versatile strategy uses non-toxic reagents without the need of metal catalysts in a sustainable solvent, being an interesting alternative to traditional hazardous protocols.
- Saavedra, Beatriz,Marset, Xavier,Guillena, Gabriela,Ramón, Diego J.
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supporting information
p. 3462 - 3467
(2020/06/04)
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- A general and practical sulfonylation of benzylic ammonium salts with sulfonyl hydrazides for the synthesis of sulfones
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A practical and efficient approach adopting transition-metal-free cross-coupling of sulfonyl hydrazides with benzyl ammonium salts has been developed to synthesize benzyl sulfones using Cs2CO3 as base under mild conditions. The protocol employs stable and easy to handle coupling partners, and is endowed with good substrate compatibility, leading to functional benzyl sulfones in good yields.
- Zhu, Haibo,Zhang, Yingying,Liu, Yishuai,Yang, Liu,Xie, Zongbo,Jiang, Guofang,Le, Zhang-Gao
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- A novel binuclear iron(III)-salicylaldazine complex; synthesis, X-ray structure and catalytic activity in sulfide oxidation
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A novel binuclear iron(III)-salicylaldazine complex has been synthesized and characterized by various techniques such as IR and UV–Vis spectroscopy and X-ray crystallography. The catalytic oxidation of sulfides in the presence of the aforementioned complex was explored at room temperature using urea hydrogen peroxide (UHP) as an oxidant. Effects of different reaction conditions consisting catalyst and oxidant amount, solvent effect and reaction time on the catalytic activity and selectivity in the reaction of methylphenylsulfide oxidation has been surveyed. Perfect selectivity toward sulfoxide was achieved after 15 min in CH3CN by choice of a properly optimized reaction condition.
- Akbari, Ali,Amini, Mojtaba,Bagherzadeh, Mojtaba,Ellern, Arkady,Mesbahi, Elnaz,Woo, L. Keith
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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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- A safe and compact flow platform for the neutralization of a mustard gas simulant with air and light
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A low footprint, mobile, robust and frugal chemical neutralization technology is reported for the oxidative neutralization of a mustard gas simulant. It relies on the inherent properties of a highly engineered continuous flow setup and carefully optimized and simple, yet robust, experimental conditions. The neutralization protocol uses only non-toxic, widely available and cheap chemicals. The continuous flow setup integrates a singlet oxygen generator and exploits its oxidative power to neutralize 2-chloroethyl ethyl sulfide (CEES), the most common thioether mustard gas simulant. The flow reactor can be connected to either pressurized oxygen or air and handles CEES as a 1 M solution in EtOH containing a trace amount (0.06 molpercent) of a non-toxic and widely available photosensitizer (Methylene Blue). Upon irradiation with visible light (orange or white light), total and highly selective neutralization towards the corresponding non-toxic sulfoxide (1-chloro-2-(ethylsulfinyl)ethane, CEESO) is obtained with reactor effluents containing less than 1percent of the corresponding potentially toxic sulfone (1-chloro-2-(ethylsulfonyl)ethane, CEESO2). With a low footprint (L × W × H 94 × 42 × 40 cm), this neutralization technology can be equipped on a vehicle for on-site interventions, localized at a neutralization facility or both. This experimental work is also supported with the computational rationalization of the reactivity of CEES towards singlet oxygen.
- Bianchi, Pauline,Emmanuel, Noémie,Legros, Julien,Monbaliu, Jean-Christophe M.
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supporting information
p. 4105 - 4115
(2020/07/30)
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- Water-soluble polymer anchored peroxotitanates as environmentally clean and recyclable catalysts for mild and selective oxidation of sulfides with H2O2 in water
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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.
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- Fe3O4?BNPs?SiO2-SO3H as a highly chemoselective heterogeneous magnetic nanocatalyst for the oxidation of sulfides to sulfoxides or sulfones
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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
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p. 36103 - 36112
(2019/11/20)
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- Method for preparing aryl sulfone compound as well as method for extracting catalyst and aryl sulfone compound
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The invention provides a preparation method of an aryl sulfone compound, which is characterized in that in an organic solvent and under an aerobic atmosphere, a catalytic system composed of a metal-ligand-TEMPO is used for catalytic oxidation of a thioether compound to obtain the aryl sulfone compound. The preparation method is simple, green, and efficient, the reaction condition is mild, and theapplication range is wide; the invention also provides a method for extracting a catalyst and the product aryl sulfone compound used in the preparation process. The ethyl acetate is added to a reaction mixture, steps of filtering and condensation under reduced pressure are carried out to obtain a filtrate and the catalyst, and silica gel column chromatography and concentration extraction are carried out to obtain the aryl sulfone compound. The extraction method is simple, and the extracted catalyst has high activity and good cycle stability, and the extraction rate of the product aryl sulfonecompound is high.
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Paragraph 0088-0091
(2019/02/13)
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- Method for photocatalytic synthesis of sulfur sulfone compounds
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The invention discloses a method for photocatalytic synthesis of sulfur sulfone compounds, and belongs to the technical field of catalysis. The invention provides a novel green environmentally-friendly method to efficiently synthesize the sulfur sulfone derivatives, and one thioether compound and an oxidizing agent are subjected to direct oxidization to form one corresponding sulfur sulfone compound under illumination by utilizing cercosporin as a catalyst. The method provided by the invention adopts the cercosporin as the catalyst, the catalytic conditions are milder, the reaction can be performed at room temperature under visible light irradiation, the catalyst has high catalytic activity and can be used for high-selectivity catalytic synthesis of the sulfur sulfone compounds, and the micro catalyst can make a yield higher, wherein the yield can reach 90% or more; and the photocatalyst and substrate raw materials used in the method are simple and easy to obtain, have low costs and can be produced on a large scale, and the method has very good application prospects.
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Paragraph 0030-0031; 0056-0068
(2019/05/15)
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- Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides
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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
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p. 3048 - 3055
(2019/03/21)
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- Switchable Synthesis of Aryl Sulfones and Sulfoxides through Solvent-Promoted Oxidation of Sulfides with O2/Air
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A practical and switchable method for the synthesis of aryl sulfones and sulfoxides via sulfide oxidation was developed. The chemoselectivities of products were simply controlled by reaction temperature using O2/air as the terminal oxidant and oxygen source. The broad substrate scope, easy realization of gram-scale production, and the simplification of a sulfide oxidation system render the strategy attractive and valuable.
- Cheng, Zhen,Sun, Pengchao,Tang, Ailing,Jin, Weiwei,Liu, Chenjiang
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supporting information
p. 8925 - 8929
(2019/11/14)
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- Controlled α-mono- and α,α-di-halogenation of alkyl sulfones using reagent-solvent halogen bonding
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The direct and selective α-mono-bromination of alkyl sulfones was achieved through base-mediated electrophilic halogenation. The appropriate combination of solvent and electrophilic bromine source was found to be critical to control the nature of the products formed, where reagent-solvent halogen bonding is proposed to control the selectivity via alteration of the effective size of the electrophilic bromine source. Conversely, the α,α-di-brominated sulfones were selectively obtained in good yields following polyhalogenation followed by selective de-halogenation during workup. Both procedures can be applied on gram scale, and the mono-halogenation was successfully extended to the fully selective α-chlorination, α-iodination and α-fluorination of alkyl sulfones.
- Poteat, Christopher M.,Lindsay, Vincent N. G.
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supporting information
p. 2912 - 2915
(2019/03/17)
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- Manganese-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols with Sulfones: A Tool to Access Highly Substituted Vinyl Sulfones
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The development of first-row-transition-metal catalysts that can match with the reactivities of the noble metals is considered to be challenging yet very much a desirable goal in homogeneous catalysis. It has become even more fascinating to develop processes where these metals show a unique reactivity and selectivity than their higher congeners. Herein, we report on the catalytic activity of a pincer complex of the abundant earth metal manganese for an unprecedented acceptorless dehydrogenative coupling of alkyl sulfones with alcohols. Thus, highly functionalized vinyl sulfones were obtained in moderate to good yields. Both benzylic and aliphatic alcohols could be utilized, and several functional groups including bromides and iodides are tolerated under the reaction conditions. The reaction is environmentally benign, producing dihydrogen and water as byproducts. Preliminary mechanistic experiments involving kinetic, deuterium-labeling, and NMR experiments were performed.
- Barman, Milan K.,Maji, Biplab,Waiba, Satyadeep
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p. 973 - 982
(2021/08/24)
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- Cercosporin-bioinspired selective photooxidation reactions under mild conditions
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The development of an efficient system for selective oxidation of organic compounds to generate more valuable compounds with molecular oxygen is a significant challenge in industrial chemistry. Bioinspired by the ability of naturally occurring perylenequinonoid pigments (PQPs) to generate reactive oxygen species (ROS) upon photoirradiation, here we report that cercosporin, one of the perylenequinonoid pigments, can function as a cost-effective and environmentally friendly photocatalyst for a wide range of selective oxidations, including benzylic C-H bonds to carbonyls, amines to aldehydes, and sulfides to sulfoxides. All of the representative reactions proceeded smoothly with high efficiency under mild conditions. Owing to the use of inexpensive metal-free visible light-driven photocatalyst produced from microbial fermentation with cheap glucose as the starting material and the ease of handling, we expect that this developed method will be particularly attractive for many more applications in synthetic transformation.
- Li, Jia,Bao, Wenhao,Tang, Zhaocheng,Guo, Baodang,Zhang, Shiwei,Liu, Haili,Huang, Shuping,Zhang, Yan,Rao, Yijian
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supporting information
p. 6073 - 6081
(2019/11/20)
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- Method for synthesizing sulfoxide compound
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The invention discloses a method for synthesizing a sulfoxide compound and belongs to the technical field of synthesis of organic compounds. The method disclosed by the invention comprises the step of catalyzing a reaction between a thioether compound and an oxygen gas agent under the condition of illumination by taking perylene bisimide as a catalyst, thereby obtaining the sulfoxide compound. According to the method, selective oxidation of thioether catalyzed by perylene bisimide under visible light is achieved for the first time, and sulfoxide derivatives are successfully constructed in high yield; and according to the method, the reaction conditions are mild, the reaction efficiency is high, the substrate applicable range is wide, the atom utilization ratio is high, the regioselectivity and chemical selectivity of reaction are high, and thus, the method has a potential application value.
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Paragraph 0103-0107
(2019/10/04)
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- Reusable BNPs-SiO2@(CH2)3NHSO3H-catalysed selective oxidation of sulfides to sulfones
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Reusable boehmite nanoparticles–silica–NHSO3H (BNPs-SiO2@(CH2)3NHSO3H) was found to be an efficient heterogeneous nanocatalyst for the selective oxidation of sulfides to sulfones in the presence of H2O2. Excellent yields, easy and quick isolation of products, short reaction times and excellent selectivity are the main advantages of this method. The catalyst was characterized using Fourier transform infrared spectroscopy, energy-dispersive X-ray analysis, X-ray diffraction, and transmission and scanning electron microscopies.
- Bahrami, Kiumars,Khodamorady, Minoo
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- Efficient molybdenum catalyzed chemoselective, solvent-free oxidation of sulfides to sulfones at room temperature
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An effcient and reusable molybdenum-based catalyst has been prepared by tethering dioxomolybdenumacetylacetonate complex, MoO2(acac)2, via postsynthesis modifcation of zeolite beta. The catalyst has been characterized by Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), scanning electron microscopy-energy dispersive X-ray analysis (SEM-EDX) and inductively coupled plasma (ICP). The catalyst exhibited very high activity for the selective oxidation of sulfdes to sulfones at room temperature. The catalyst can be recycled and reused four times without signifcant loss of activity.
- Hadigavabar, Ali Dadashi,Tabatabaeian, Khalil,Zanjanchi, Mohammad Ali,Mamaghani, Manouchehr
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p. 3829 - 3833
(2018/05/24)
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- Fe3O4/PEG-SO3H as a heterogeneous and magnetically-recyclable nanocatalyst for the oxidation of sulfides to sulfones or sulfoxides
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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
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p. 1757 - 1761
(2018/02/09)
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- Oxidation of Organosulfides to Organosulfones with Trifluoromethyl 3-Oxo-1λ 3,2-benziodoxole-1(3 H)-carboxylate as an Oxidant
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An alternative approach is described for the oxidation of organosulfides to the corresponding organosulfones by using trifluoromethyl 3-oxo-1λ 3,2-benziodoxole-1(3 H)-carboxylate as an oxidant. The oxidation of the sulfides was performed by using 2.4 equivalents of the oxidant in refluxing acetonitrile. The oxidation products were isolated in good to excellent yields.
- Mangaonkar, Saeesh R.,Kole, Priyanka B.,Singh, Fateh V.
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supporting information
p. 199 - 202
(2017/09/28)
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- Oxidation reactions catalysed by molybdenum(VI) complexes grafted on UiO-66 metal–organic framework as an elegant nanoreactor
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A heterogeneous catalyst was synthesized by immobilizing Mo(CO)3 in a UiO-66 metal–organic framework. The benzene ring of the organic linker in UiO-66 was modified via liquid-phase deposition of molybdenum hexacarbonyl, Mo(CO)6, as starting precursor to form the (arene)Mo(CO)3 species inside the framework. The structure of this catalyst was characterized using X-ray diffraction, and chemical integrity was confirmed using Fourier transform infrared and diffuse reflectance UV–visible spectroscopic methods. The metal content was analysed with inductively coupled plasma. Field emission scanning electron microscopy was used to measure particle size and N2 adsorption measurements to characterize the specific surface area. This catalytic system was efficiently applied for epoxidation of alkenes and oxidation of sulfides. The Mo-containing metal–organic framework was reused several times without any appreciable loss of its efficiency.
- Afzali, Niloufar,Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah,Mechler, Adam,Mohammadpoor-Baltork, Iraj,Kardanpour, Reihaneh,Zadehahmadi, Farnaz
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- Heptamolybdate: A highly active sulfide oxygenation catalyst
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The sulfide oxygenation activities of both heptamolybdate ([Mo7O24]6-, [1]6-) and its peroxo adduct [Mo7O22(O2)2]6- ([2]6-) were examined in this contribution. [Mo7O22(O2)2]6- was prepared in a yield of 65% from (NH4)6[Mo7O24] (1a) upon treatment of 10 equiv. of H2O2 and structurally identified through single crystal X-ray diffraction study. (nBu4N)6[Mo7O22(O2)2] (2b) is an efficient catalyst for the sequential oxygenation of methyl phenyl sulfide (MPS) by H2O2 to the corresponding sulfoxide and subsequently sulfone with a 100% utility of H2O2. Surprisingly, (nBu4N)6[Mo7O24] (1b) is a significantly faster catalyst than 2b for MPS oxygenation under identical conditions. The pseudo-first order kcat constants from initial rate kinetics are 54 M-1 s-1 and 19 M-1 s-1 for 1b and 2b, respectively. Electrospray ionization mass spectrometry (ESI-MS) investigation of 1b under the catalytic reaction conditions revealed that [Mo2O11]2- is likely the main active species in sulfide oxygenation by H2O2.
- Porter, Ashlin G.,Hu, Hanfeng,Liu, Xuemei,Raghavan, Adharsh,Adhikari, Sarju,Hall, Derrick R.,Thompson, Dylan J.,Liu, Bin,Xia, Yu,Ren, Tong
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p. 11882 - 11887
(2018/09/10)
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- MANUFACTURING METHOD OF COMPOUND HAVING SULFONYL GROUP
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The present invention relates to a method for manufacturing a compound having a sulfonyl group, which includes a step for reacting thiosulfonates in a solvent comprising nucleophilic bases with an electrophilic agent. Accordingly, the present invention can manufacture the compound having the sulfonyl group with a variety of structures with high efficiency and high yield through more simplified processes than conventional methods.COPYRIGHT KIPO 2018
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Paragraph 0107-0109; 0115
(2018/10/03)
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- Remote Nucleophilic Allylation by Allylrhodium Chain Walking
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Metal migration through a carbon chain is a versatile method for achieving remote functionalization. However, almost all known examples involve the overall net migration of alkylmetal species. Here, we report that allylrhodium species obtained from hydrorhodation of 1,3-dienes undergo chain walking toward esters, amides, or (hetero)arenes over distances of up to eight methylene units. The final, more highly conjugated allylrhodium species undergo nucleophilic allylation with aldehydes and with an imine to give Z-homoallylic alcohols and amines, respectively.
- Groves, Alistair,Martínez, Jose I.,Smith, Joshua J.,Lam, Hon Wai
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supporting information
p. 13432 - 13436
(2018/09/21)
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- Synthesis of new oxido-vanadium complexes: Catalytic properties and cytotoxicity
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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
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- Synthesis, characterization, spectral and catalytic activity of tetradentate (NNNO) azo-imine Schiff base copper(II) complexes
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The hexadentate ligand, 2,2′-bis(salicylideneamino)azobenzene, 1 has been synthesized from 2,2′-diaminoazobenzene and salicylaldehyde in refluxing diethyl ether. Reaction of ligand 1 with Cu(II) acetate and Cu(II) perchlorate separately in methanol afforded tetradentate (N,N,N,O) Cu(II) complexes, Cu(L) & [Cu(HL)]ClO4 respectively [where H2L represent the one imine moiety cleavage product of ligand 1 (H represents the dissociable amino and phenolic protons)]. These were characterized by microanalytical data and spectroscopic studies. In addition, the crystal structures of the ligand 1 and complexes Cu(L) & [Cu(HL)]ClO4 were determined by X-ray diffraction analysis. The diffraction analysis revealed that the ligand (H2L) binds Cu(II) centers in (N,N,N,O) tetra dentate fashion in distorted square planer geometry. In complex [Cu(HL)]ClO4 the apical position of copper center is weakly coordinated with one perchlorate ion. The dimeric structure of the molecule [Cu(HL)]ClO4 is stabilized through NH2···O hydrogen bonds. The fluorescence and redox property of ligand 1 and complexes Cu(L) & [Cu(HL)]ClO4 were studied. Preliminary DFT calculations were carried out using crystallographic coordinates to understand the electronic spectra and redox properties of the ligand and complexes. The complex Cu(L) shows very good catalytic activities towards oxidation of benzyl alcohol to benzaldeyhde (under solvent-free condition) and organic thioethers to sulfoxide and sulfones using H2O2 as the oxidant.
- Pratihar, Jahar Lal,Mandal, Paritosh,Brand?o, Paula,Mal, Dasarath,Felix, Vitor
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p. 221 - 228
(2018/05/22)
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