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• 3019-20-3 isopropylthiobenzene 
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Relevant academic research and scientific papers

Exploiting Substrate Diversity for Preparing Synthetically Valuable Sulfoxides via Asymmetric Hydrogenative Kinetic Resolution

A detailed study is disclosed on the Rh-mediated hydrogenative kinetic resolution of α,β-unsaturated sulfoxides with alkyl and aryl substituents at the α-, E- and Z-positions of the double bond. This stereoselective catalytic methodology has enabled the p

Palladium-Catalyzed Enantioselective Alkenylation of Sulfenate Anions

A novel approach to synthesize enantio-enriched alkenyl/aryl sulfoxides is achieved by using CsF to generate sulfenate anions and conducting the catalytic enantioselective alkenylation with [Pd(allyl)Cl]2/(2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene (SL-J002-1). A wide variety of sulfoxides bearing sensitive functional groups are produced with high yields (up to 94%) and enantioselectivities (up to 92%).

Palladium/PC-Phos-Catalyzed Enantioselective Arylation of General Sulfenate Anions: Scope and Synthetic Applications

Herein we reported an efficient palladium-catalyzed enantioselective arylation of both alkyl and aryl sulfenate anions to deliver various chiral sulfoxides in good yields (up to 98%) with excellent enantioselectivities (up to 99% ee) by the use of our developed chiral O,P-ligands (PC-Phos). PC-Phos are easily prepared in short steps from inexpensive commercially available starting materials. The single-crystal structure of the PC4/PdCl2 showed that a rarely observed 11-membered ring was formed via the O,P-coordination with the palladium(II) center. The salient features of this method include general substrate scope, ease of scale-up, applicable to the late-stage modification of bioactive compounds, and the synthesis of a marketed medicine Sulindac.

Method for catalyzing asymmetric oxidation of sulfur ether

The invention provides a method for asymmetrically oxidizing sulfur ether. The sulfur ether is subjected to asymmetric catalytic oxidation reaction by taking a chiral complex formed by a four-tooth nitrogen organic ligand and a metal scandium compound as a catalyst and taking hydrogen peroxide as an oxidizing agent to obtain a corresponding chiral sulfoxide compound, and the yield and the enantioselectivity are more than 90 percent. The reaction has the advantages of cleanness, mild reaction condition, high conversion rate and high enantioselectivity. The method has an industrial prospect.

Multivariate Metal-Organic Frameworks as Multifunctional Heterogeneous Asymmetric Catalysts for Sequential Reactions

The search for versatile heterogeneous catalysts with multiple active sites for broad asymmetric transformations has long been of great interest, but it remains a formidable synthetic challenge. Here we demonstrate that multivariate metal-organic frameworks (MTV-MOFs) can be used as an excellent platform to engineer heterogeneous catalysts featuring multiple and cooperative active sites. An isostructural series of 2-fold interpenetrated MTV-MOFs that contain up to three different chiral metallosalen catalysts was constructed and used as efficient and recyclable heterogeneous catalysts for a variety of asymmetric sequential alkene epoxidation/epoxide ring-opening reactions. Interpenetration of the frameworks brings metallosalen units adjacent to each other, allowing cooperative activation, which results in improved efficiency and enantioselectivity over the sum of the individual parts. The fact that manipulation of molecular catalysts in MTV-MOFs can control the activities and selectivities would facilitate the design of novel multifunctional materials for enantioselective processes.

Chiral DHIP-Based Metal-Organic Frameworks for Enantioselective Recognition and Separation

Two chiral porous 2,3-dihydroimidazo[1,2-a]pyridine (DHIP)-based metal-organic frameworks (MOFs) are assembled from an enantiopure dipyridyl-functionalized DHIP bridging ligand. The Zn-DHIP MOF shows a good enantioseparation performance toward aromatic sulfoxides, and the heterogeneous adsorbent can be readily recovered and reused without significant degradation of the separation performance.

Engineering chiral Fe(salen)-based metal-organic frameworks for asymmetric sulfide oxidation

Two chiral porous Fe(salen)-based metal-organic frameworks are constructed and are shown to be efficient and recyclable heterogeneous catalysts for asymmetric oxidation of sulfides to sulfoxides with an enantioselectivity of up to 96%.

A chiral porous metallosalan-organic framework containing titanium-oxo clusters for enantioselective catalytic sulfoxidation

A chiral porous zeolite-like metal-organic framework is constructed by using mixed ligands of dipyridyl-functionalized chiral Ti(salan) and biphenyl-4,4′-dicarboxylate. The framework containing salan-bound Ti 4O6 clusters consists of both hydrophobic and amphiphilic mesocages and is shown to be an efficient and recyclable heterogeneous catalyst for the oxidation of thioethers to sulfoxides by aqueous H2O 2 (up to 82% ee), displaying markedly enhanced enantioselectivity over the homogeneous catalyst by providing a cavity confinement effect. This work highlights the potential of significantly improving enantioselectivity of homogeneous catalysts by using MOFs as support structures.

Titanium-salan-catalyzed asymmetric sulfoxidations with H2O 2: Design of more versatile catalysts

Titanium-salan complexes with 3,3'-diphenyl substituents in the salicylidene rings of the salan ligand are efficient sulfoxidation catalysts, capable of catalyzing the asymmetric oxidation of bulky aryl benzyl sulfides with H2O2 with good to high enantioselectivities. In this paper, substituent effects on titanium-salan-catalyzed enantioselective oxidation of sulfides to sulfoxides have been systematically investigated. Titanium-salan catalysts with halogen substituents at the 5,5'-positions (3,3'-H2dihydrogen substituted) have been found to catalyze the oxidation of both bulky aryl benzyl sulfides and small alkyl phenyl sulfides with good to high enantioselectivities. Kinetic data witness a direct attack of the sulfide to the electrophilic active oxygen species; a consistent reaction mechanism is proposed. Copyright 2013 John Wiley & Sons, Ltd. Titanium-salan complexes with halogen substituents at the 5,5'-positions are versatile catalysts for the oxidation of both bulky aryl benzyl sulfides and small alkyl phenyl sulfides, demonstrating good to high chemoselectivity (up to 92 %) and enantioselectivity (up to 93 % ee). Copyright

Chiral microporous Ti(salan)-based metal-organic frameworks for asymmetric sulfoxidation

Chiral porous metal-metallosalan frameworks are constructed from an unsymmetrical chiral pyridinecarboxylate ligand derived from Ti(salan) and are shown to be heterogeneous catalysts for asymmetric oxidation of thioethers to sulfoxides.