890127-34-1

Upstream product

• 2633-67-2 4-vinylbenzenesulfonyl chloride 
• 35132-20-8 (R,R)-1,2-diphenylethylenediamine 

Downstream Products

• 1612842-85-9 C₂₆H₃₃N₂O₅PS₃ 
• 1612842-79-1 C₃₀H₄₁N₂O₅PS₃ 
• 1612842-81-5 C₃₂H₄₅N₂O₅PS₃ 
• 1612842-88-2 C₂₈H₃₇N₂O₅PS₃ 
• 1612842-84-8 C₃₄H₄₉N₂O₅PS₃ 
• 1434647-83-2 (R,R)-N′-4′-vinylbenzyl-N-4-vinylbenzenesulfonyl-1,2-diphenylethylene-1,2-diamine 

Relevant academic research and scientific papers

Synthesis of polymer-immobilized TsDPEN ligand and its application in asymmetric transfer hydrogenation of cyclic sulfonimine

Crosslinked polymers containing chiral N-sulfonylated diamine (TsDPEN) structure were synthesized by radical polymerization of chiral N 1-(4-vinylbenzenesulfonyl)-1,2-diphenylethylene-1,2-diamine, divinylbenzene and achiral vinyl monomer. The p

Superhydrophobic, chiral, and mesoporous TsDPEN copolymer coordinated to ruthenium species as an efficient catalyst for asymmetric transfer hydrogenation

Homogeneous chiral catalysts usually show higher catalytic activities than corresponding heterogeneous chiral catalysts, because of their easy interaction between catalytically active sites with reactant molecules. We demonstrate here superhydrophobic, chiral, and mesoporous catalysts (TsDPEN-Ru) synthesized from copolymerization of N-p-styrenesulfonyl-1,2-diphenylethylenediamine (V-TsDPEN) with divinylbenzene and loading of Ru species exhibiting much higher activities in asymmetric transfer hydrogenation (ATH) of ketones in aqueous solution than corresponding homogeneous chiral catalyst. This phenomenon is strongly related to the unique features of high enrichment for the reactants in superhydrophobic TsDPEN-Ru catalysts due to their good wettability, as well as easy transfer of product from the catalyst into water phase. These features open a door for design and developing a wide variety of chiral catalysts for asymmetric catalysis.

Preparation and catalytic performances of a molecularly imprinted RU-complex catalyst with an NH2 binding site on a SiO2 surface

A catalyst surface with an active metal site, a shape-selective reaction space, and an NH2 binding site for o-fluorobenzophenone was designed and prepared by the molecular imprinting of a supported metal complex on a SiO2 surface. A ligand of a SiO2-supported Ru complex that has a similar shape to the product of o-fluorobenzophenone hydrogenation was used as a template. An NH2 binding site for o-fluorobenzophenone was spatially arranged on the wall of a molecularly imprinted cavity with a similar shape to the template. The structures of the SiO2-supported and molecularly imprinted Ru catalysts were characterized in a step-by-step manner by means of solid-state magic angle spinning (MAS) NMR, XPS, UV/Vis, N 2 adsorption, XRF, and Ru K-edge EXAFS. The molecularly imprinted Ru catalyst exhibited excellent shape selectivity for the transfer hydrogenation of benzophenone derivatives. It was found that the NH2 binding site on the wall of the molecularly imprinted cavity enhanced the adsorption of o-fluorobenzophenone, of which the reduction product was imprinted, whereas there was no positive effect in the case of o-methylbenzophenone, which cannot interact with the NH2 binding site through hydrogen bonding. Tailoring a pocket: A molecularly imprinted Ru-complex catalyst with an NH 2 binding site for o-fluorobenzophenone has been successfully designed and prepared on a SiO2 surface for shape-selective transfer hydrogenation (see scheme). Copyright

Preparation of surface molecularly imprinted Ru-complex catalysts for asymmetric transfer hydrogenation in water media

Molecularly imprinted Ru-complex catalysts acting in water were prepared on a SiO2 surface by molecular imprinting of a SiO2- supported Ru-complex using organic polymers as surface matrix overlayers. (R)-1-(o-fluorophenyl)ethanol, which is one of the hydrogenated products of o-fluoroacetophenone, was imprinted on the supported Ru-complex as a template, and an active Ru-complex with a shape-selective reaction space (molecularly imprinted cavity) was prepared inside the wall of the hydrophobic organic polymer matrix overlayers. Structures of the SiO2-supported and molecularly imprinted Ru catalysts were characterized by means of solid-state NMR, XPS, XRF, ICP, UV/vis, XAFS, TGA, and SEM. The molecularly imprinted Ru catalysts exhibited fine shape selectivity and enantioselectivity for the asymmetric transfer hydrogenation of o-fluoroacetophenone and its derivatives.

Synthesis of polymer microspheres functionalized with chiral ligand by precipitation polymerization and their application to asymmetric transfer hydrogenation

Monodisperse, crosslinked poly(divinylbenzene) and poly(methacrylic acid-co-ethylene glycol dimethacrylate) microspheres with (1R,2R)-N 1-toluenesulfonyl-1,2-diphenylethylene-1,2-diamine ((R,R)-TsDPEN) moiety were successfully prepared by precipitation polymerization. Introduction site of the (R,R)-TsDPEN moiety into the polymer microspheres could be controlled by changing the order of addition of the corresponding monomers. The functionalized polymer microspheres were applied to asymmetric transfer hydrogenation of ketone and imine. Polymer microsphere-supported chiral catalysts showed good reactivity and enantioselectivity in the catalytic asymmetrie transfer hydrogenations. Chiral secondary alcohol was quantitatively obtained with 94% ee in the asymmetric transfer hydrogenation of acetophenone in water. We also found that introduction site of the chiral catalyst and hydrophobiclty of the microspheres, as well as degree of the crosslinking, affected the yield and enantioselectivity of chiral product in this reaction.

Asymmetric transfer hydrogenation of imines catalyzed by a polymer-immobilized chiral catalyst

The asymmetric transfer hydrogenation of imines was performed with the use of a polymer-immobilized chiral catalyst. The chiral catalyst, prepared from crosslinked polystyrene-immobilized chiral 1,2-diamine monosulfonamide, was effective in the asymmetric transfer hydrogenation of N-benzyl imines in CH 2Cl2 to give a chiral amine in high yield and good enantioselectivity. Furthermore, an amphiphilic polymeric catalyst prepared from crosslinked polystyrene containing sulfonated groups successfully catalyzed the asymmetric transfer hydrogenation of cyclic imines in water. Enantioenriched secondary amines with up to 94% ee were obtained by using a polymeric catalyst.

Asymmetric transfer hydrogenation of aromatic ketones in water using a polymer-supported chiral catalyst containing a hydrophilic pendant group

Hydrophilic polymers having pendant groups of carboxylates or sulfonates have been used as a polymer support for chiral 1,2-diamine monosulfonamides. The polymeric chiral complex prepared from the polymer-supported chiral ligand with ruthenium dichloride·p-cymene was used in the asymmetric transfer hydrogenation of prochiral ketones in water. The balance between hydrophilicity and hydrophobicity of the polymer support influenced both the reactivity and the enantioselectivity of the reaction in water. The chiral polymeric complex having a quaternary ammonium salt structure as the pendant group worked well in water. In most cases the polymer-supported catalyst having a quaternary ammonium sulfonate pendant group showed superior enantioselectivity compared to the corresponding non-supported model catalyst in the solution system. The polymeric catalysts can be reused without loss of catalytic activity.