3698-95-1Relevant academic research and scientific papers
Methyl-transfer reaction to alkylthiol catalyzed by a simple vitamin B 12 model complex using zinc powder
Pan, Ling,Tahara, Keishiro,Masuko, Takahiro,Hisaeda, Yoshio
, p. 194 - 199 (2011)
The catalytic methyl-transfer reaction from methyl tosylate to 1-octanethiol was carried out in the presence of a simple vitamin B12 model complex, [Co(III){(C2C3)(DO)(DOH)pn}Br 2], with zinc powder as the reducing reagent at 50°C. Such a catalytic reaction proceeded via the formation and dissociation of a cobalt-carbon bond in the simple vitamin B12 model complex under non-enzymatic conditions. The mechanism for the methyl-transfer reaction was investigated by electronic and mass spectroscopies. The Co(I) species, which is generated from the reduction of the catalyst by the zinc powder, and its methylated CH3-Co complex were found to be indispensable intermediates.
Electrochemical methyl-transfer reaction to alkylthiol catalyzed by hydrophobic vitamin B12
Pan, Ling,Shimakoshi, Hisashi,Hisaeda, Yoshio
, p. 26 - 27 (2009)
The catalytic methyl-transfer reaction from methyl tosylate to 1-octanethiol was carried out in the presence of heptamethyl cobyrinate perchlorate, hydrophobic vitamin B12, under electrochemical conditions at -1.0 V vs. Ag/AgCl using a carbon-f
Synthesis of Aryl Methyl Sulfides from Arysulfonyl Chlorides with Dimethyl Carbonate as the Solvent and C1 Source
Miao, Ren-Guan,Qi, Xinxin,Wu, Xiao-Feng
supporting information, p. 5219 - 5221 (2021/10/19)
A new procedure for the synthesis of aryl methyl sulfides from dimethyl carbonate (DMC) and arylsulfonyl chlorides has been achieved. In this strategy, DMC plays a dual role as both, C1 building block and green solvent. Arylsulfonyl chlorides served as the sulfur precursors, and a variety of aryl methyl sulfides were obtained in moderate to excellent yields with good functional group tolerance. Additionally, alkylsulfonyl chloride and dibenzyl carbonate are proven to be suitable substrates as well.
Synthesizing process of flutriafol key intermediate 1-(2-fluorophenyl)-1-(4-fluorophenyl)ethylene oxide
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Paragraph 0013; 0014, (2019/02/25)
The invention discloses a synthesizing process of a flutriafol key intermediate 1-(2-fluorophenyl)-1-(4-fluorophenyl)ethylene oxide. The synthesizing process comprises the following steps: mixing 1-bromooctane and sodium methyl mercaptide, adding tetrabutylammonium bromide, stirring for reacting, adding water for standing and layering to form an organic phase and a water phase after the reaction is finished, performing skimming to remove the water phase, washing the organic phase with water, performing drying and suction filtration, dissolving a prepared product and dimethyl sulfate in an organic solvent for reacting, and removing the organic solvent from a reaction solution to obtain sulfur-onium salt after the reaction is finished; adding the sulfur-onium salt, inorganic alkali and 2,4'-difluoro benzophenone into a solvent, stirring for reacting, adding water for standing and layering to form an organic phase and a water phase after the reaction is finished, performing skimming to remove the water phase, washing the organic phase with water, performing dehydration, drying and suction filtration, and removing the solvent from filtrate to obtain the 1-(2-fluorophenyl)-1-(4-fluorophenyl)ethylene oxide. By adopting the synthesizing process, the alkali is screened, and sodium hydroxide is taken as an alkali medium, thereby improving the reaction yield; moreover, methyl n-octyl sulfide has low odor.
Sulfonium salt type chloramine antibacterial agent and synthetic method thereof
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Paragraph 0038; 0039, (2018/11/22)
The invention belongs to the technical field of chemical synthesis and application of chloramine antibacterial agents, and provides a sulfonium salt type chloramine antibacterial agent and a syntheticmethod thereof. A preparation method of the antibacterial agent comprises the following steps: taking bromoalkyl 5,5-dimethylhydantoin and thioether as raw materials to prepare a sulfonium salt bromide chloramine precursor compound IV; reacting the precursor compound IV with t-butyl hypochlorite at normal temperature after ion exchange to obtain an antibacterial agent compound I. The antibacterial agent disclosed by the invention introduces a cationic structural unit-sulfonium salt group into a hydrophobic chain chloramine group, so that water solubility of the chloramine antibacterial agentis greatly improved and structure stability of the chloramine antibacterial agent is significantly enhanced. By using staphylococcus aureus as a model strain, the antibacterial test result shows thatthe bactericidal activity of the prepared sulfonium salt type chloramine compound is better than that of a mono-quaternary ammonium salt type chloramine compound.
The energy-transfer-enabled biocompatible disulfide–ene reaction
Teders, Michael,Henkel, Christian,Anh?user, Lea,Strieth-Kalthoff, Felix,Gómez-Suárez, Adrián,Kleinmans, Roman,Kahnt, Axel,Rentmeister, Andrea,Guldi, Dirk,Glorius, Frank
, p. 981 - 988 (2018/08/31)
Sulfur-containing molecules participate in many essential biological processes. Of utmost importance is the methylthioether moiety, present in the proteinogenic amino acid methionine and installed in tRNA by radical-S-adenosylmethionine methylthiotransferases. Although the thiol–ene reaction for carbon–sulfur bond formation has found widespread applications in materials or medicinal science, a biocompatible chemo- and regioselective hydrothiolation of unactivated alkenes and alkynes remains elusive. Here, we describe the design of a general chemoselective anti-Markovnikov hydroalkyl/aryl thiolation of alkenes and alkynes—also allowing the biologically important hydromethylthiolation—by triplet–triplet energy transfer activation of disulfides. This fast disulfide–ene reaction shows extraordinary functional group tolerance and biocompatibility. Transient absorption spectroscopy was used to study the sensitization process in detail. The hereby gained mechanistic insights were successfully employed for optimization of the catalytic system. This photosensitized transformation should stimulate bioimaging applications and carbon–sulfur bond-forming late-stage functionalization chemistry, especially in the context of metabolic labelling.
Hydrogenation of sulfoxides to sulfides under mild conditions using ruthenium nanoparticle catalysts
Mitsudome, Takato,Takahashi, Yusuke,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
supporting information, p. 8348 - 8351 (2014/08/18)
The first demonstration of the hydrogenation of sulfoxides under atmospheric H2 pressure is reported. The highly efficient reaction is facilitated by a heterogeneous Ru nanoparticle catalyst. The mild reaction conditions enable the selective hydrogenation of a wide range of functionalized sulfoxides to the corresponding sulfides. The high redox ability of RuO x nanoparticles plays a key role in the hydrogenation.
Highly efficient deoxygenation of sulfoxides using hydroxyapatite-supported ruthenium nanoparticles
Takahashi, Yusuke,Mitsudome, Takato,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
supporting information, p. 420 - 422 (2014/04/17)
We report the first example of the deoxygenation of sulfoxides using heterogeneous catalysts with alcohols as environmentally friendly reducing reagents. Hydroxyapatitesupported Ru nanoparticles (RuNPs/HAP) act as a highly efficient and reusable heterogeneous catalyst for deoxygenation of sulfoxides using alcohols as reductants. The catalytic activity of Ru nanoparticles is outstanding compared to other metal nanoparticles such as Pt, Pd, Rh, and Au nanoparticles. RuNPs/HAP can also catalyze the selective deoxygenation of various sulfoxides, giving the corresponding sulfides in excellent yields.
One-pot reduction of sulfoxides with NaBH4, CoCl2. 6H2O catalyst, and moist alumina
Yakabe, Shigetaka,Hirano, Masao,Morimoto, Takashi
experimental part, p. 2251 - 2255 (2011/06/27)
Sulfoxides are reduced by a combination of sodium borohydride, a catalytic amount of cobalt(II) chloride hexahydrate, and chromatographic neutral alumina preloaded with a small amount of water (moist alumina) in hexane to produce the corresponding sulfides in good to excellent yields under mild conditions. An interesting structural influence of sulfoxides on their reactivity is observed. Copyright
Dimethyl carbonate as an ambident electrophile
Tundo, Pietro,Rossi, Laura,Loris, Alessandro
, p. 2219 - 2224 (2007/10/03)
(Chemical Equation Presented) The features of various anions having different soft/hard character (aliphatic and aromatic amines, alcohoxydes, phenoxides, thiolates) are compared with regard to nucleophilic substitutions on dimethyl carbonate (DMC), using different reaction conditions. Results are well in agreement with the Hard-Soft Acid-Base (HSAB) theory. Accordingly, the high selectivity of monomethylation of CH2 acidic compounds and primary aromatic amines with DMC can be explained by two different subsequent reactions, which are due to the double electrophilic character of DMC. The first step consists of a hard-hard reaction and selectively produces a soft anion, which, in the second phase, selectively transforms into the final monomethylated product, via a soft-soft nucleophilic displacement (yield >99% at complete conversion, using DMC as solvent).
