- 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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- Oxidation of Dithia Compounds: Comparative Experimental and Theoretical Studies on 1,3-Bis(methylthio)propane, Bis(methylthio)methane, and meso-4,6-Dimethyl-1,3-dithiane
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1,3-Bis(methylthio)propane, bis(methylthio)methane, and meso-4,6-dimethyl-1,3-dithiane were oxidized with 1–4 equivalents of hydrogen peroxide, meta-chloroperbenzoic acid, sodium periodate, or potassium permanganate, respectively, and the amounts of oxidized substrates (sulfoxides and/or sulfones) were determined by NMR spectroscopy. Sulfanyl groups in the former starting material turned out to behave like independent functions, while a mutual influence of the sulfur functions was verified in the latter compounds. A meaningful investigation was possible in the conformationally constrained dithiane derivative. Oxidation of the dithiane with stoichiometric amounts of periodate led to exclusive formation of bissulfoxides, while hydrogen peroxide and meta-chloroperbenzoic acid yielded the possible products less specifically and permanganate preferentially furnished sulfones. The experimental investigations were supported by calculations on energies and stereoelectronic effects of starting materials, products, and transition states. The unique property of permanganate to exclusively yield sulfones might be due to its special oxidation mechanism, where the sulfur is not only acting as nucleophile, but concomitantly as electrophilic moiety.
- González, Victorino Vallejos,Podlech, Joachim
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p. 5430 - 5442
(2021/10/25)
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- Metal-free radical thiolations mediated by very weak bases
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Aromatic thioethers and analogous heavier chalcogenides were prepared by reaction of arene-diazonium salts with disulfides in the presence of the cheap and weak base NaOAc. The mild and practical reaction conditions (equimolar reagents, DMSO, r.t., 8 h) tolerate various functional groups (e.g. Br, Cl, NO2, CO2R, OH, SCF3, furans). Mechanistic studies indicate the operation of a radical aromatic substitution mechanism via aryl, acetyloxyl, thiyl, and dimsyl radicals.
- Koziakov, Denis,Majek, Michal,Jacobi Von Wangelin, Axel
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supporting information
p. 11347 - 11352
(2016/12/16)
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- Selective oxidation of sulfides to sulfoxides by a molybdate-based catalyst using 30% hydrogen peroxide
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An efficient method is reported for selective oxidation of various types of sulfides to sulfoxides and sulfones in good to high yields using 30% H 2O2 in the presence of catalytic amounts of molybdate-based catalyst in acetonitrile as solvent at room temperature. The catalyst can be easily recovered and reused for seven reaction cycles without considerable loss of activity.
- Bayat, Ahmad,Shakourian-Fard, Mehdi,Hashemi, Mohammad Mahmoodi
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- Application of silica vanadic acid as a heterogeneous, selective and highly reusable catalyst for oxidation of sulfides at room temperature
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Silica vanadic acid (vanadium has been supported on silica) is applied as an efficient, highly reusable and heterogeneous catalyst for the selective oxidation of sulfide to sulfoxide using hydrogen peroxide and in the acetonitrile as a solvent at room temperature. The catalyst can be easily recovered and reused for ten reaction cycles without considerable loss of activity. Also, some advantages of this method were applicable at large scales, high TON of catalyst, chemoselectivity, easy work-up and short reaction time.
- Zolfigol, Mohammad Ali,Khazaei, Ardeshir,Safaiee, Maliheh,Mokhlesi, Mohammad,Rostamian, Rahele,Bagheri, Mahsa,Shiri, Morteza,Kruger, Hendrik Gerhardus
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- Uronium hydrogen sulfate/urea-hydrogen peroxide as a green and metal-free catalytic system for the efficient, chemo-, and homoselective oxidation of sulfides to sulfoxides
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Chemical Equation Presented An efficient, chemoselective, and metal-free oxidation of sulfides is described using urea-hydrogen proxide (UHP) adduct as a stable, inexpensive, and easily handled reagent in the presence of uronium hydrogen sulfate (UHS). Both UHP and UHS release urea as an environmentally benign byproduct. The advantages of the described method are generality, chemoselectivity, short reaction time, low cost, high atom economy, and green chemistry protocols. Copyright Taylor & Francis Group, LLC.
- Hasaninejad, Alireza,Chehardoli, Gholamabbas,Zolfigol, Mohammad Ali,Abdoli, Abbas
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experimental part
p. 271 - 280
(2011/04/22)
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- Metal-free catalytic oxidation of sulfides to sulfoxides with ammonium nitrate, ammonium hydrogen sulfate and ammonium bromide as catalyst
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A general and metal-free catalytic oxidation of aliphatic and aromatic sulfides to their corresponding sulfoxides via combination of ammonium nitrate (NH4NO3), supported ammonium hydrogen sulfate on silica gel (NH4HSO4-sio2and a catalytic amount of ammonium bromide (NH4Br) in the presence of wet sio2 (50percent, w/w) has been investigated. The reactions were carried out heterogeneously and selectively in short reaction times in CH2Cl2 at room temperature. This protocol is mild and efficient compared to other reported methods.
- Ghorbani-Choghamarani, Arash,Zolfigol, Mohammad Ali,Ayazi-Nasrabadi, Roia
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experimental part
p. 33 - 36
(2010/08/19)
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- Structure-activity relationships for selected sulfur-rich antifungal compounds
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A series of sulfur compounds has been prepared and tested against two kinds of fungi: Aspergillus niger and Aspergillus flavus. Results on various sulfone disulfides and ester disulfides have led to the formulation of a proposed mechanism for fungicidal behaviour that permits one to anticipate which structures will be antifungal.
- Baerlocher, Felix Jakob,Langler, Richard Francis,Frederiksen, Mathias Ugelstad,Georges, Noni Mandissa,Witherell, Ross Davidson
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p. 167 - 172
(2007/10/03)
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- Microbiological transformations 36: Preparative scale synthesis of chiral thioacetal and thioketal sulfoxides using whole-cell biotransformations
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This work describes the preparative scale enantioselective oxidation of some prochiral dithioacetals and dithioketals to their corresponding chiral monosulfoxides using whole-cell cultures of microorganisms.
- Alphand, Veronique,Gaggero, Nicoletta,Colonna, Stefano,Pasta, Piero,Furstoss, Roland
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p. 9695 - 9706
(2007/10/03)
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- Sulfoxide derivative and process for its preparation
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A novel sulfoxide derivative of the general formula STR1 wherein R1 and R3 are the same or different, and each represents and alkyl group having 1 to 4 carbon atoms, a phenyl group or a halo- or methyl-substituted phenyl group, R2 is a hydrogen atom, a lower alkyl group, benzyl group, or a p-methoxy- or p-bromo-benzyl group, R1 and R2, together, may form an alkylene group containing 3 carbon atoms, and X is an oxygen or sulfur atom, and to a process for its preparation.
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