67501-03-5

Upstream product

• 109-72-8 n-butyllithium 
• 16491-20-6 (R)-1-methyl-4-(phenylsulfinyl)benzene 
• 78347-74-7 N-<(S)-1-(o-hydroxyphenyl)ethyl>-N-<(S)-1-α-naphthylethyl> (S^R)-phenylsulfinamide 
• 1126-80-3 (n-butylthio)benzene 
• 13153-10-1 1-(butylsulfinyl)benzene 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 77382-90-2 (S)-o-<1-((S)-1-α-naphtylethylamino)ethyl>phenol 
• 78347-74-7 N-<(S)-1-(o-hydroxyphenyl)ethyl>-N-<(S)-1-α-naphthylethyl> (S^S)-phenylsulfinamide 
• 4972-29-6 benzenesulphinyl chloride 
• 1307296-47-4 (R,S)-N-benzyl-N-(1-phenylethyl)benzenesulfinamide 
• 939962-74-0 bis(2,2’-bromophenyl) sulfoxide 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 1191-47-5 dibutylmagnesium 

Relevant academic research and scientific papers

Bio-inspired single-chain polymeric nanoparticles containing a chiral salen TiIV complex for highly enantioselective sulfoxidation in water

A series of bio-inspired single-chain polymeric nanoparticles (SCPNs) containing a chiral salen TiIV complex in their hydrophobic cavity were constructed from the synthesized amphiphilic copolymers of poly(NIPAAm-co-IL/Ti(salen)) (NIPAAm, N-isopropylacrylamide; IL/Ti(salen), vinylimidazolium ionic liquid-modified chiral salen TiIV complex). These SCPNs behaved as enzyme-mimetic catalysts due to compartmentalization and site isolation, mediating enantioselective oxidation of various sulfides in water with excellent yields (90-99%) and enantioselectivities (ee, 88-99%). In particular, the ee values observed for electron-rich substrates (>95% ee) represented the best results so far in titanium-salen systems. Moreover, the catalysts could be easily recovered for steady reuse by thermo-controlled separation due to thermo-responsive properties. This work first constructed titanium-containing biomimetic SCNPs for biocatalysis of enantioselective sulfoxidation in water.

Ionic liquid-functionalized amphiphilic Janus nanosheets afford highly accessible interface for asymmetric catalysis in water

High oil/water interfacial area together with accessible interfaces for regents is the key to achieving efficient asymmetric catalysis in water. Herein, by taking advantage of the excellent interfacial activity of Janus nanosheets (JNS), as well as the unique compatibility of imidazolium ionic liquid (IL), we developed a series of IL-functionalized amphiphilic Janus mesosilica nanosheets which afford highly accessible reaction interfaces for highly enantioselective sulfoxidation in water. The JNS-typed chiral salen TiIV catalysts were prepared by selectively decorating hydrophobic chiral salen TiIV complex on one side of Janus mesosilica nanosheets through the imidazolium-based IL linker. Benefiting from the two-dimensional porous Janus structure, as well as the compatible IL linker, the IL-tagged JNS catalysts afforded high oil/water interfacial areas and highly accessible reaction interface for sulfides and H2O2, significantly accelerating asymmetric sulfoxidation in water using H2O2 as an oxidant. In addition, they can be facilely recovered for stable reuse by simple centrifugation.

Light-controlled cooperative catalysis of asymmetric sulfoxidation based on azobenzene-bridged chiral salen TiIVcatalysts

Incorporation of azobenzene into the linker of bimetallic chiral salen TiIVcatalysts allowed the photoswitchable arrangement of the two Ti(salen) units throughcis/transphotoisomerization of azobenzene. The differently arranged Ti(salen) units changed their cooperative function to reflect the positional relationships, as a result, their efficiency as cooperative catalysts in asymmetric sulfoxidation could be readily controlled by light stimuli.

An ionic liquid-functionalized amphiphilic Janus material as a Pickering interfacial catalyst for asymmetric sulfoxidation in water

Ionic liquid-functionalized amphiphilic Janus chiral salen TiIV catalysts were prepared by partial hydrophobic modification of silica with a chiral salen TiIV complex through an imidazolium ionic liquid (IL) linker. By optimizing their hydrophobic/hydrophilic balance, the IL-functionalized JNP materials exhibited excellent interfacial activity, significantly accelerating asymmetric sulfoxidation in water through the formation of stable Pickering emulsions. Moreover, catalyst recovery was readily achieved using centrifugation.

Titanium(iv)-folded single-chain polymeric nanoparticles as artificial metalloenzyme for asymmetric sulfoxidation in water

Intrachain TiIV-oxazoline complexation together with hydrophobic interaction triggered the self-folding of an oxazoline-containing single polymeric chain in water. The formed TiIV-folded single-chain polymeric nanoparticles (SCPNs) acted as metalloenzyme-mimetic catalysts in asymmetric sulfoxidation in water owing to their organized, compartmentalized structure, effective site isolation, and also secondary coordination sphere provided by a copolymer backbone. In addition, they also could be facilely recovered for reuse by simple thermo-controlled separation.

ION PAIR CATALYSIS OF TUNGSTATE AND MOLYBDATE

D The present invention relates to ion pair catalysts (I) comprising the cationic bisguanidinium ligand (A) and diperoxomolybdate anion (B). The present invention also relates to ion pair catalysts (III) comprising the cationic bisguanidinium ligand (C) and peroxotungstate anion (D). It further relates to the use of the said catalysts in the manufacture of enantiomerically enriched sulfoxides.

Enantioselective Sulfoxidation Catalyzed by a Bisguanidinium Diphosphatobisperoxotungstate Ion Pair

The first enantioselective tungstate-catalyzed oxidation reaction is presented. High enantioselectivities were achieved for a variety of drug-like phenyl and heterocyclic sulfides under mild conditions with H2O2, a cheap and environmentally friendly oxidant. Synthetic utility was demonstrated through the preparation of (S)-Lansoprazole, a commercial proton-pump inhibitor. The active ion-pair catalyst was identified to be bisguanidinium diphosphatobisperoxotungstate using Raman spectroscopy and computational studies.

Symmetric diarylsulfoxides as asymmetric sulfinylating reagents for dialkylmagnesium compounds

At -78 °C, primary dialkylmagnesium compounds reacted with diarylsulfoxides when 1.5 equiv of the dilithium salt of (S)-BINOL was added as a promotor. Alkyl aryl sulfoxides resulted in up to quantitative yield and with up to 97% ee. This demonstrates the feasibility of asymmetric sulfinylations by achiral sulfinylating agents (from the perspective of Alkyl2Mg) as well as the feasibility of asymmetric sulfoxide-magnesium exchanges (from the perspective of Ar2SO).

Iron-catalyzed imidative kinetic resolution of racemic sulfoxides

Kinetic resolution of racemic sulfoxides requires either custom substrates or shows moderate enantioselectivity, leading to achiral coproducts (such as sulfones) as an intrinsic part of the process. A new strategy is demonstrated that allows the resolution of racemic sulfoxides through catalytic asymmetric nitrene-transfer reactions. This approach gives rise to both optically active sulfoxides and highly enantioenriched sulfoximines. By using a chiral iron catalyst and a readily available iodinane reagent, high selectivity factors have been achieved under very practical reaction conditions. With respect to the substrate scope, it is noteworthy that this unprecedented imidative kinetic resolution of racemic sulfoxides provides access to both aryl-alkyl and dialkyl sulfoximines in highly enantioenriched forms. Copyright

Application of a novel 1,3-diol with a benzyl backbone as chiral ligand for asymmetric oxidation of sulfides to sulfoxides

A chiral 1,3-diol with a benzyl backbone has been used for the asymmetric oxidation of sulfides to sulfoxides. Moderate to good yields and enantioselectivity (upto 87% ee) have been observed.