30506-35-5

Upstream product

• 542-69-8 1-iodo-butane 
• 109-72-8 n-butyllithium 
• 72784-68-0 trimethylsilyl 4-methylbenzenesulfinate 
• 693-03-8 n-butyl magnesium bromide 
• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 693-04-9 butyl magnesium bromide 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 1774-35-2 di(p-tolyl) sulfoxide 
• 1191-47-5 dibutylmagnesium 
• 443640-88-8 (S_S,S_S)-2-phenyl-1,1-di-p-tolylsulfinyl-ethylene 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 1307296-48-5 (R,S)-N-Benzyl-N-(1-phenylethyl)-p-toluenesulfinamide 
• 10439-23-3 4-methylbenzenesulfinyl chloride 

Downstream Products

• 21784-96-3 n-butyl 4-methylphenyl sulfide 
• 20288-49-7 (S)-1-(butylsulfinyl)-4-methylbenzene 
• 620-84-8 4-methyldiphenylamine 
• 30506-35-5 (R)-1-(butylsulfinyl)-4-methylbenzene 

Relevant academic research and scientific papers

The remarkable effect of methanol on sulfide photooxidations. Evidence for its dual reactivity

The addition of small amounts of methanol to photooxidation mixtures of sulfides dramatically enhances sulfone in preference to sulfoxide formation. High concentrations of methanol on the other hand have the opposite effect of promoting sulfoxide in prefe

cis-Carbocuperation of acetylenic sulfoxides and corresponding applications in the regio- and stereoselective synthesis of polysubstituted vinyl sulfoxides

cis-Carbocuperation reaction of monoorganocopper reagent with acetylenic sulfoxides, followed by electrophilic reaction with a variety of electrophiles, provided a regio- and stereoselective method to prepare the versatile polysubstituted vinyl sulfoxides

Synthesis and reactions of exo-camphorylsulfonyloxaziridine

The first example of an exo-camphorylsulfonyloxaziridine 4a was prepared by m-CPBA oxidation of camphor imine 9. This surprising result is due to the conformation of the imine which apparently prevents attack of the peracid from the endo direction. Simila

Highly efficient and selective aqueous aerobic oxidation of sulfides to sulfoxides or sulfones catalyzed by tungstate-functionalized nanomaterial

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.

Development of a simple high-throughput assay for directed evolution of enantioselective sulfoxide reductases

We report on the development of high-throughput fluorogenic assay that can streamline directed evolution of enantioselective sulfoxide reductases. As a model, methionine sulfoxide reductase A (MsrA) has been evolved to expand its limited substrate scope. The resulting mutant MsrA can resolve a range of new challenging racemic sulfoxides with high efficiency including the pharmaceutically relevant albendazole sulfoxide. The simplicity and the level of throughput make this method also suitable for the screening of metagenomic libraries in future for the discovery of new enzymes with similar reactivities.

Ullmann-type: N-arylation of anilines with alkyl(aryl)sulfonium salts

A palladium/copper-cocatalyzed Ullmann-type N-arylation of anilines using alkyl(aryl)sulfonium triflates as arylation reagents has been accomplished. The reaction enabled Caryl-S bond cleavage over Calkyl-S bond breakage of alkyl(aryl)sulfoniums by Pd(P(tBu)3)2/CuI and gave the corresponding N-arylated products in good to high yields. It was also significant that the reactions of aniline with asymmetric butyl(mesityl)(aryl)sulfonium triflates showed excellent selectivity, in which the aryl groups other than the bulky and electron-rich mesityl moieties were transformed.

Selective Late-Stage Oxygenation of Sulfides with Ground-State Oxygen by Uranyl Photocatalysis

Oxygenation is a fundamental transformation in synthesis. Herein, we describe the selective late-stage oxygenation of sulfur-containing complex molecules with ground-state oxygen under ambient conditions. The high oxidation potential of the active uranyl cation (UO22+) enabled the efficient synthesis of sulfones. The ligand-to-metal charge transfer process (LMCT) from O 2p to U 5f within the O=U=O group, which generates a UV center and an oxygen radical, is assumed to be affected by the solvent and additives, and can be tuned to promote selective sulfoxidation. This tunable strategy enabled the batch synthesis of 32 pharmaceuticals and analogues by late-stage oxygenation in an atom- and step-efficient manner.

Sulfoxide and sulfone compounds, as well as selective synthesis method and application thereof

The invention discloses a method for selectively synthesizing a sulfoxide compound shown as a formula (II) and a sulfone compound shown as a formula (III). In a reaction solvent, thioether (I) is usedas a reaction raw material and oxygen as an oxidation reagent, under the catalytic action of visible light and a photosensitive reagent; under the assistance of an additive, when a large-polarity proton-containing additive such as an acid and an alcohol or a solvent or an additive with excellent electron donating ability is used, a sulfoxide compound (II) is selectively generated; and when a small-polarity aprotic additive or a solvent is used, a sulfone compound (III) is selectively generated. The synthesis method has the advantages of easily available and cheap raw materials, simple reaction operation, mild reaction conditions, high yield and excellent functional group tolerance. According to the invention, synthesis and modification of some medicines are realized, and an efficient method for selectively constructing sulfoxide and sulfone compounds is provided for medicinal chemistry research.

Chiral Br?nsted-Acid-Catalyzed Asymmetric Oxidation of Sulfenamide by Using H2O2: A Versatile Access to Sulfinamide and Sulfoxide with High Enantioselectivity

Herein, we describe an example of catalytic asymmetric synthesis of sulfinamides. Aromatic sulfenamides were chosen as useful substrates, because of the indispensable N-H bond, which could form an efficient hydrogen bond with chiral phosphoric acid. Hsub

Simple low cost porphyrinic photosensitizers for large scale chemoselective oxidation of sulfides to sulfoxides under green conditions: Targeted protonation of porphyrins

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.