112456-63-0

Upstream product

• 940-12-5 p-nitrophenyl methyl sulfoxide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 75-16-1 methylmagnesium bromide 
• 701-57-5 1-methylthio-4-nitro-benzene 
• 164021-74-3 (1S,2R)-(-)-2-[N-(3’,5’-di-tert-butylsalicylidene)amino]-1,2-diphenylethanol 

Downstream Products

• 125761-96-8 (R)-(+)-Methyl <(4-nitrophenyl)sulfinyl>acetate 

Relevant academic research and scientific papers

Asymmetric Oxidation of Sulfides with Molecular Oxygen Catalyzed by β-Oxo Aldiminato Manganese(III) Complexes

Enantioselective aerobic oxidation of sulfides with combined use of molecular oxygen and pivalaldehyde afforded the optically active sulfoxides using β-oxo aldiminato manganese(III) complex catalysts.For example, 2-chlorophenyl methyl sulfide afforded opt

Asymmetric sulfoxidation of thioethers with hydrogen peroxide in water mediated by platinum chiral catalyst

Easy stereoselective oxidation of prochiral aryl alkyl sulfides 2 to the corresponding sulfoxides can be achieved in water-surfactant medium with inexpensive hydrogen peroxide mediated by the chiral platinum diphosphine complex {[(R)-BINAP]Pt(μ-OH)}2

Synthesis of novel β-amino alcohols and their application in the catalytic asymmetric sulfoxidation of sulfides

Novel chiral norephedrine-based β-amino alcohol ligands containing a thiophene ring were prepared from norephedrine and substituted furan carbaldehydes (methyl- or ethyl-substituted) and used in combination with VO(acac)2 for the asymmetric oxidation of aryl methyl sulfides using H2O2 as an oxidant. Amino alcohol derived Schiff bases 4,5a-b gave higher enantiomeric excesses than amino alcohol-derived reduced Schiff based ligands 6,7a-b. Of these chiral ligands, (1S,2R)-5b and (1S,2R)-7b gave high yields (90%) with moderate to high enantioselectivities (78%, 96% ee, respectively). The oxidation of other aryl methyl sulfides with (1S,2R)-5b and (1S,2R)-7b as ligands afforded the corresponding sulfoxides in 60-89% yields and with 92-99% ee.

Cooperative chiral salen TiIV catalyst supported on ionic liquid-functionalized graphene oxide accelerates asymmetric sulfoxidation in water

A cooperative chiral salen TiIV catalyst was prepared by covalently appending multiple chiral salen TiIV complexes on a graphene oxide (GO) surface through a flexible ionic liquid (IL) linker. Characterization results confirmed the decoration of intact Ti(salen) units on the edges and planes of exfoliated GO with the imidazolium-IL spacer. The IL-functionalized GO nanosheets endowed the chiral salen TiIV catalyst with high water-dispersion, diminished diffusion limitation, and particularly a reinforced intramolecular cooperative effect. The cooperative catalyst was thus highly efficient and universally applicable in the catalysis of asymmetric sulfoxidation in water, affording high yields of various chiral sulfoxides with excellent enantioselectivities, while traditional chiral salen TiIV complex was far less active. More importantly, the heterogeneous catalyst was perfectly stable and could be reused several times without significant loss of activity and selectivity.

Asymmetric oxidation of sulfides using (salen)manganese(III) complex as a catalyst

Asymmetric oxidation of sulfides was examined by using (salen)manganese(III) complexes as catalysts and (8S,8'S,1''S,2''S)-complex (3b) was found to show high asymmetric induction up to 90% ee. To be interested, however, (8R,8'R,1''S,2''S)-complex (1a) that showed excellent asymmetric induction in the epoxidation of simple olefins was a poor catalyst for the oxidation of sulfides.

Cooperative chiral salen TiIV catalysts with built-in phase-transfer capability accelerate asymmetric sulfoxidation in water

A series of cooperative chiral salen TiIV catalysts with inherent phase-transfer capability were prepared by covalently bridging double chiral salen TiIV units with various polyethylene glycol (PEG)-based dicationic ionic liquid (IL) linkers. Characterization results suggested the presence of polyether-based IL spacers and intact active sites in the catalysts. The polyether-based dicationic IL spacer not only enforced an intramolecular, cooperative reaction pathway favored for the asymmetric suloxidation, but also endowed the bimetallic catalysts with built-in phase transfer capability. High yields of chiral sulfoxides (in the range of 74-90%) with excellent ee values (in the range of 85-91%) were achieved within 45 min when the asymmetric oxidation of methyl phenyl sulfide, methyl p-methoxyphenyl sulfide, and methyl o-methoxyphenyl sulfide were performed in water. The catalytic efficiency was significantly higher than that over neat complex (yields, 10-16% and ee values, 77-79%). More attractively, the phase transfer catalysts could be facilely recovered by solvent precipitation for efficient reuse.

Enantioselective Aerobic Oxidation of Sulfides Catalyzed by Optically Active β-Oxo Aldiminatomanganase(III) Complexes

Enantioselective aerobic oxidation of sulfides into optically active sulfoxides was achieved by using pivalaldehyde in the presence of a catalytic amount of optically active β-oxo aldiminatomanganese(III) complexes.An acylperoxomanganese complex, formed f

Preparation of chiral oxovanadium (IV) Schiff base complex functionalized by ionic liquid for enantioselective oxidation of methyl aryl sulfides

Chiral oxovanadium (IV) Schiff base complex covalently grafted with ionic liquid (IL: 1-(3-aminopropyl)-3-methylimidazolium tetrafluoroborate) has been reported first time. The IL-functionalized complex was found to be an efficient catalyst in the enantioselective oxidation of methyl aryl sulfides to sulfoxides with hydrogen peroxide as an oxidant. Especially, the IL-functionalized complex could be recovered conveniently by simple precipitation with addition of hexane and reused at least six cycles without loss of activity and enantioselectivity.

Asymmetric oxidation of sulfides by hydrogen peroxide catalyzed by chiral manganese porphyrins in water/methanol solution

An efficient asymmetric oxidation of sulfides catalyzed by water-soluble chiral manganese porphyrin was carried out in presence of cheap and environmentally benign oxidant H2O2 at 25 °C. Prochiral sulfides were converted to respective sulfoxides with up to 100% conversion and up to 57% enantiomeric excess. The present study demonstrated the necessity of water as solvent and imidazole as co-catalyst. Application to the preparation of the optically drug, sulindac, was demonstrated.

First enantioselective iron-porphyrin-catalyzed sulfide oxidation with aqueous hydrogen peroxide

The asymmetric oxidation of sulfides by H2O2 to give optically active sulfoxides (ee up to 90%) was carried out in methanol and water using chiral water-soluble iron porphyrins as catalysts.