6378-07-0Relevant academic research and scientific papers
Tungstate supported on magnetic ionic liquid-modi?ed graphene oxide as an efficient and recyclable catalyst for the selective oxidation of sulfides
Dabiri, Minoo,Tavil, Hassan Esmaielie,Lehi, Noushin Farajinia,Movahed, Siyavash Kazemi,Mnachekanian Salmasi, Aram,Souri, Sepideh
, (2021/11/30)
An effective and recyclable catalyst based on tungstate ion immobilization on magnetic ionic liquid modified graphene oxide (WO4@Fe3O4/GO-IL) has been synthesized in this research. The catalyst was characterized by various
Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst
Zhao, Bin,Hammond, Gerald B.,Xu, Bo
supporting information, (2021/09/13)
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.
A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent
Anselmi, Silvia,Liu, Siyu,Kim, Seong-Heun,Barry, Sarah M.,Moody, Thomas S.,Castagnolo, Daniele
supporting information, p. 156 - 161 (2021/01/14)
A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.
Enzymatic kinetic resolution of chiral sulfoxides-an enantiocomplementary approach
Nosek, Vladimír,Mí?ek, Ji?í
supporting information, p. 10480 - 10483 (2019/09/07)
A new enzymatic assay for the preparation of chiral sulfoxides that is enantiocomplementary to the known (S)-enantiomer-reducing activity of methionine sulfoxide reductase A (MsrA) is described. To this end, we have utilized the enzyme DMSO reductase (DmsABC), recently discovered by us being highly upregulated in stationary phase E. coli bacteria.
Simple low cost porphyrinic photosensitizers for large scale chemoselective oxidation of sulfides to sulfoxides under green conditions: Targeted protonation of porphyrins
Mojarrad, Aida G.,Zakavi, Saeed
, p. 768 - 781 (2018/02/14)
Aerobic photooxidation of sulfides with the diacids of meso-tetra(phenyl)porphyrin, H2TPP (acid = CF3COOH, Cl2CHCOOH, HClO4 and H2SO4) under sunlight in acetonitrile gave the corresponding sulfoxides as nearly the exclusive product. The photocatalytic activity of the dications decreased as H4TPP(ClO4)2 ? H4TPP(Cl2CHCOO)2 ? H4TPP(CF3COO)2 > H4TPP(HSO4)2. Also, H4TPP(ClO4)2 and H4TPP(Cl2CHCOO)2 showed a remarkably increased oxidative stability in comparison with the free base porphyrin. The singlet oxygen quantum yield (φΔ) of the porphyrin diacids was found to be dependent on the acid used for the protonation of H2TPP. The solvent effect on the efficiency of the oxidation reaction was investigated using acetonitrile, 1,2-dichloroethane (DCE) and toluene. The higher conversions achieved in acetonitrile and DCE are in accord with the higher singlet oxygen lifetime in these solvents. Also, the lower fluorescence quantum yield of porphyrin dications in acetonitrile relative to that in DCE was used to explain the higher efficiency of the former. The porphyrin diacids can also accelerate the oxidation reaction through an acid catalysis mechanism. Also, cooxidation of methyl phenyl sulfide and diphenyl sulfide was conducted to provide insights into the nature of the active intermediates involved in the oxidation of sulfides to sulfoxides and partial overoxidation of the sulfoxides to sulfones. The results showed much higher reactivity of the persulfoxide intermediate compared to that of singlet oxygen. The catalytic system was successfully employed to the large scale preparation of sulfoxides from the corresponding sulfides under mild conditions.
Selective oxidation method of thioether
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Paragraph 0046; 0047; 0048, (2018/09/20)
The invention relates to a selective oxidation method of thioether, and discloses a novel synthesis method of a single sulfone compound shown as a formula (I). According to the invention, thioether shown in a formula (II) is taken as a raw material, under existence of tert-butyl hydroperoxide, an oxidation reaction is carried out in a solvent, after the reaction is completed, and through post-treatment, the single sulfone compound shown as the formula (I) is obtained. Compared with the prior art, an oxidizing agent tert-butyl hydroperoxide which is friendly to environment is employed, usage ofa metal catalyst is avoided, the reaction condition is mild, selectivity is high, the operation is simple, the applicability is wide, and the reaction yield is high.
Oxygenation of sulfides catalysed by SBA-15-immobilized molybdenum(VI) complex of a bis(phenol) diamine ligand using aqueous hydrogen peroxide as a green oxidant
Saberikia, Iraj,Safaei, Elham,Karimi, Babak,Lee, Yong-Iii
, (2018/03/21)
A highly efficient and reusable molybdenum-based catalyst has been synthesized by covalent grafting of a bis(phenol) diamine ligand, namely 2-(((2-bromoethyl)(2-((3,5-di-tert-butyl-2-hydroxybenzyl)amino)ethyl)amino)methyl)-4,6-di-tert-butylphenol, onto functionalized ordered mesoporous silica (SBA-15) followed by complexation with MoO2(acac)2. The resulting organic–inorganic hybrid material was found to be a highly effective catalyst for oxygenation of various sulfides to their corresponding sulfoxides or sulfones. The catalyst was characterized using transmission and scanning electron microscopies, X-ray photoelectron, Fourier transform infrared and atomic absorption spectroscopies, Brunauer–Emmett–Teller surface area analysis and thermogravimetric analysis. Mild reaction conditions, high selectivity and easy recovery and reusability of the catalyst render the presented protocol very useful for addressing industrial needs and environmental concerns.
Iron(III) Amine Bis(phenolate) Complex Immobilized on Silica-Coated Magnetic Nanoparticles: A Highly Efficient Catalyst for the Oxidation of Alcohols and Sulfides
Karimpour, Touraj,Safaei, Elham,Karimi, Babak,Lee, Yong-Ill
, p. 1889 - 1899 (2018/01/04)
We aimed to immobilize a complex of iron(III) amine bis(phenolate) on silica-coated magnetic nanoparticles as a new magnetically recoverable catalyst (Fe3O4@SiO2-APTES-FeLGDC). Both the chemical nature and the structure of catalyst were confirmed by using field-emission transmission electron microscopy, field-emission scanning electron microscopy, FTIR spectroscopy, thermogravimetric analysis, vibrating sample magnetometry, X-ray photoelectron spectroscopy, XRD, atomic absorption spectroscopy, and elemental analysis. This sustainable catalyst leads to the efficient oxidation of a wide range of alcohols and sulfides with excellent conversion and selectivity under a mild conditions to their corresponding oxidized products, acids (or ketones) and sulfoxides, respectively. Furthermore, the stability of the structure and morphology of our efficient recyclable system was investigated, and all of the data proved that the complex was anchored firmly to the magnetite nanoparticles.
Asymmetric Sulfinylations of N-Methylephedrine-Modified Tri- or Tetraalkyl Zincates by Symmetric Diaryl Sulfoxides
Ruppenthal, Simon,Brückner, Reinhard
, p. 2518 - 2530 (2018/06/11)
Diethylzinc was treated with 1 or 2 equiv. of AlkMgCl or PhMgBr (preferably) or with 1 equiv. of nBuLi (less efficiently) for forming species – plausibly zincates – which were sulfinylated by diaryl sulfoxides to give racemic alkyl aryl sulfoxides in yields reaching 100 %. Dialkylzinc reagents were also activated by treatments with 1 or 2 equiv. of an enantiomerically pure alkylmagnesium β-aminoalkoxide. This worked best when the alkoxide stemmed from a dialkylmagnesium reagent and an equimolar amount of N-methyl-(–)-ephedrine. This second activation mode allowed sulfinylations of what was originally the dialkylzinc reagent with diaryl sulfoxides. This generated alkyl aryl sulfoxides with enantiomeric ratios up to 93:7 in up to 100 % yield.
Supported vanadium Schiff bases complex on nano silica: a heterogeneous catalyst for the selective oxidation of sulfides and alcohols
Dabiri, Minoo,Koohshari, Majid,Shafipour, Fazeleh,Kasmaei, Melika,Salari, Parinaz,MaGee, David
, p. 1265 - 1272 (2016/06/09)
Abstract: A vanadium Schiff base complex on nano silica was prepared by reaction of nano silica NH2-functionalized, 2,4-dihydroxy benzaldehyde and VO(acac)2. The VSBC@NS was used as an efficient and reusable heterogeneous catalyst fo
