7144-49-2Relevant academic research and scientific papers
Divergent S- And C-Difluoromethylation of 2-Substituted Benzothiazoles
Wang, Xiu,Ye, Wenchao,Kong, Taige,Wang, Chenlu,Ni, Chuanfa,Hu, Jinbo
supporting information, p. 8554 - 8558 (2021/11/13)
Two unprecedented and complementary synthetic strategies for S- and C-difluoromethylation of 2-substituted benzothiazoles have been developed by taking advantage of the remarkably different reactivity of CF2H- and 2-PySO2CF2- nucleophiles. A variety of structurally diverse difluoromethyl 2-isocyanophenyl sulfides and 2-difluoromethylated benzothiazoles were synthesized with these two new synthetic protocols.
Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y
Thierry, Thibault,Pfund, Emmanuel,Lequeux, Thierry
supporting information, p. 14826 - 14830 (2021/10/01)
A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.
Stereoselective Synthesis of C, C-Glycosides from exo-Glycals Enabled by Iron-Mediated Hydrogen Atom Transfer
Tardieu, Damien,Desnoyers, Marine,Laye, Claire,Hazelard, Damien,Kern, Nicolas,Compain, Philippe
supporting information, p. 7262 - 7267 (2019/10/11)
We describe herein a convenient strategy for the construction of C,C-glycoside building blocks via the intermediacy of tertiary pseudoanomeric radicals. Application of an iron-mediated hydrogen atom transfer/Michael-Giese coupling enables the anomeric quaternization of readily available exo-glycals with good to complete stereocontrol in the pyranose and furanose series. Carefully optimized conditions allow the use of challenging trisubstituted derivatives prone to undergo further elaboration to stable neoglycoconjugates. Preliminary results for direct C-disaccharide synthesis are also discussed.
Oxidative kinetic resolution of heterocyclic sulfoxides with a porphyrin-inspired manganese complex by hydrogen peroxide
Yang, Jinchuang,Wang, Lianyue,Lv, Ying,Li, Ning,An, Yue,Gao, Shuang
supporting information, p. 156 - 159 (2017/12/15)
We have successfully reported here the low loading porphyrin-inspired high-valent manganese (IV)-oxo complex was applied in oxidative kinetic resolution (OKR) of racemic heterocyclic sulfoxides using the environmentally benign hydrogen peroxide for the first time. This approach allows for rapid OKR (0.5 h) of a variety of racemic sulfoxides (including pyridine, pyrimidine, pyrazine, thiazole, benzothiazole, thiophene) in excellent enantioselectivity (up to > 99% ee), simultaneously generating the corresponding sulfones in high yield (up to 80%). The catalytic system also showed an unexceptionable chemoselectivity for the sulfoxide substrates with hydroxyl groups in which only the sulfoxide group was oxidized. The practical utility of the method has been demonstrated in the OKR of gram-scale sulfoxides.
Kinetic Modelling of the catalytic oxidation of 2-(methylmercapto)-benzothiazole under mild conditions
Córdoba,Saux,Pierella
, p. 173 - 180 (2017/07/27)
2-(Methylmercapto)-benzothiazole oxidation was performed over Copper modified zeolites. The microporous materials were synthesized by the hydrothermal crystallization method and later modified with metal incorporation by wet impregnation. The solid cataly
Sulfone compound (by machine translation)
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Paragraph 0042, (2017/10/06)
[Problem] to safely and conveniently, highly selective, sulfide compound producing a sulfone compound. [Solution] pH is 9 - 12 under, water or water-insoluble solvent or an aromatic hydrocarbon-based solvent mixture, sodium hypochlorite is used as oxidizing agent, (1) (2) from the compound represented by the formula sulfide sulfone compound represented by the formula manufacturing method. (R1 And R2 Are each independently an alkyl, aryl, aralkyl, heteroaryl)[Drawing] no (by machine translation)
Radical Fluoroalkylation of Isocyanides with Fluorinated Sulfones by Visible-Light Photoredox Catalysis
Rong, Jian,Deng, Ling,Tan, Ping,Ni, Chuanfa,Gu, Yucheng,Hu, Jinbo
, p. 2743 - 2747 (2016/02/26)
The radical fluoroalkylation of isocyanides with fluorinated sulfones is enabled by visible-light photoredox catalysis. A wide range of readily available mono-, di-, and trifluoromethyl heteroaryl sulfones can thus be used as efficient radical fluoroalkylation reagents under mild conditions. This method not only describes a new synthetic application of fluorinated sulfones, but also provides a new route to fluoroalkyl radicals.
Active potassium niobates and titanoniobates as catalysts for organic sulfide remediation
Saux, Clara,Leal Marchena, Candelaria,Dinamarca, Robinson,Pecchi, Gina,Pierella, Liliana
, p. 58 - 61 (2016/01/09)
Pure (KNbO3) and titanium-substituted (KTi0.1Nb0.9O3 and KTi0.2Nb0.8O3) potassium niobates with perovskite crystalline structures were prepared, characterized and tested as catal
Transition metal-modified polyoxometalates supported on carbon as catalyst in 2-(methylthio)-benzothiazole sulfoxidation
Frenzel, Romina A.,Romanelli, Gustavo P.,Blanco, Mirta N.,Pizzio, Luis R.
, p. 123 - 132 (2015/03/30)
Polyoxometalates with lacunary Keggin structure modified with transition metal ions [PW11O39 M(H2O)]5-, where M = Ni2+, Co2+, Cu2+ or Zn2+, were synthesized and supported on activated carbon to obtain the PW11MC catalysts. Using FT-IR and DTA-TGA it was concluded that the [PW11O39M(H2O)]5- species are interacting with the functional groups of the support, and that thermal treatment leads to the loss of the coordinatively bonded water molecules without any noticeable anion degradation. The activity and selectivity of the catalysts in the sulfoxidation reaction of 2-(methylthio)-benzothiazole, an emerging environmental pollutant, were evaluated. The reaction was carried out in acetonitrile as solvent using H2O2 35% p/v as a clean oxidant. The conversion values decreased in the following order: PW11NiC > PW11CuC > PW11CoC > PW11ZnC, with selectivity to sulfoxide higher than 69%. The catalyst could be reused without appreciable loss of the catalytic activity at least three times. The materials were found to be efficient and recyclable catalysts for 2-(methylthio)-benzothiazole sulfoxidation in order to obtain a more biodegradable product than the corresponding substrate. [Figure not available: see fulltext.]
Carbon-supported metal-modified lacunary tungstosilicic polyoxometallates used as catalysts in the selective oxidation of sulfides
Frenzel, Romina,Sathicq, ángel G.,Blanco, Mirta N.,Romanelli, Gustavo P.,Pizzio, Luis R.
, p. 27 - 36 (2015/04/14)
Lacunary tungstosilicic polyoxometallates modified with transition metal ions [SiW11O39M(H2O)]6-, where M = Mn2+, Fe2+, Co2+or Cu2+, were synthesized and supported on activated carbon to obtain the SiW11MC catalysts. The samples were characterized by FT-IR, XRD, N2 adsorption-desorption measurements, and the acidic properties were determined using the isopropanol dehydration test reaction. The activity and selectivity of the catalysts were evaluated in the selective oxidation of a series of sulfides to sulfoxides or sulfone. The reaction was carried out in acetonitrile as solvent using H2O2 35% p/V as a clean oxidant. The conversion values decreased in the following order: SiW11MnC > SiW11FeC > SiW11CuC > SiW11CoC. The catalysts were reused without appreciable loss of their catalytic activity. It was found that the activity of the catalysts decreases in parallel with the increment in the reduction temperature values. The most easily reducible catalyst displayed the highest conversion values. We found a convenient and selective procedure for oxidizing sulfides to sulfoxides or sulfones using aqueous hydrogen peroxide and a catalytic amount of lacunary tungstosilicic polyoxometallates supported on carbon at low temperatures (20-50 °C) in a reasonably short reaction time
