6099-21-4

Usage

Uses

Used in Organic Synthesis:
1,2-Bis(phenylsulfinyl)ethane is used as a chiral ligand in asymmetric synthesis for its ability to catalyze a variety of reactions, particularly in the formation of carbon-carbon and carbon-nitrogen bonds. Its effectiveness in these processes contributes to the development of enantioselective reactions, which are crucial for producing chiral compounds with specific biological activities.
Used in Pharmaceutical Applications:
Due to its unique stereochemical properties, 1,2-Bis(phenylsulfinyl)ethane has been studied for its potential pharmaceutical applications. It can be utilized as a chiral auxiliary in various organic reactions, which is important for the synthesis of biologically active compounds with desired stereochemistry. This can lead to the development of new drugs with improved efficacy and selectivity.
Used in Research and Development:
1,2-Bis(phenylsulfinyl)ethane is also used in research and development for studying the mechanisms of asymmetric catalysis and the influence of chiral auxiliaries on reaction stereochemistry. Understanding these aspects can help in designing new synthetic routes and improving existing ones, ultimately leading to more efficient and selective chemical processes.

Upstream product

• 622-20-8 1,2-bis(phenylthio)ethane 
• 20451-53-0 Phenyl vinyl sulfoxide 
• 87330-63-0 1,1,2,2-tetramethyl-1,2-disilacyclohexa-3,5-diene 
• 31268-20-9 bromomethyl phenyl sulfoxide 
• 13456-86-5 3,5-Dichloro-2,4,6-trimethyl-benzonitrile N-oxide 
• 7722-84-1 dihydrogen peroxide 
• 3111-52-2 potassium thiophenolate 
• 108-98-5 thiophenol 
• 107-21-1 ethylene glycol 
• 931-59-9 benzenesulfenyl chloride 

Downstream Products

• 622-20-8 1,2-bis(phenylthio)ethane 
• 1403825-13-7 Pd(1,2-bis(phenylsulfinyl)ethane)(trifluoroacetate)₂ 
• 21461-90-5 (meso)-1,2-bis(phenylsulfinyl)ethane 

Relevant academic research and scientific papers

Thermodynamic Resolution and Enantioselective Synthesis of C2-Symmetric Bis-sulfoxides Based on Chiral Iridium(III) Complexes

Enantiopure λ-[Ir(dfppy)2(MeCN)2](PF6) and Δ-[Ir(dfppy)2(MeCN)2](PF6) (where dfppy is (4,6-difluoropheny)pyridine) were demonstrated to preferentially react with (S,S)-1,2-bis(arylsulfinyl)

Carbazole-triazine based donor-acceptor porous organic frameworks for efficient visible-light photocatalytic aerobic oxidation reactions

We report the synthesis of a series of carbazole-triazine based donor-acceptor (D-A) POFs and their photocatalytic activities for aerobic oxidation reactions. The simultaneous introduction of a carbazole-based electron donor and a triazine-based electron acceptor in D-A POFs stabilizes the charge transfer state and enables an efficient triplet-triplet energy transfer to generate 1O2. Meanwhile, systematic variation of the D-A distance results in the tunable photoredox properties and consequently the efficiency for generation of reactive oxygen species (ROSs). Upon visible light excitation, all three D-A POFs exhibit excellent capability to promote three aerobic oxidations: sulfide oxidation, oxidative amine coupling, and Mannich reactions. This systematic study validates the design principle of D-A POFs as high-performance photo-oxidation catalysts with wide substrate scope and excellent stability and recyclability.

A Bulky Disulfoxide Ligand for Pd-Catalyzed Oxidative Allylic C-H Amination with 2,2,2-Trichloroethyl Tosyl Carbamate

Challenging substrates and conditions in homogeneous catalysis pose stringent demands on the ligands used. A novel, bulky, 1-adamantyl-substituted disulfoxide ligand designed after a systematic evaluation of the electronic and steric properties of disulfoxide substituents permits the allylic oxidative C-N coupling reaction to proceed at lower catalyst loading while requiring a smaller excess of reagents. Additionally, this ligand improves the yields when TsNHCOOCH2CCl3, a novel reagent that permits deprotection of the products under both acidic and basic conditions, is used.

Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides

Metal- and additive-free oxidation of a series of sulfides/thioketones has been achieved using cyclic diacyl peroxides as mild oxygen sources. This protocol features simple manipulation, high chemo- and diastereoselectivity, and a broad substrate scope (up to 42 examples), tolerates many common functional groups, and is scalable and applicable to the late-stage sulfoxidation strategy. A preliminary mechanistic study by quantum mechanical calculations suggests that a single two-electron transfer process is energetically more favorable, and indicates the reactivity of cyclic diacyl peroxides distinct from conventional acyclic acyl peroxides.

Catalytic intermolecular allylic C-H alkylation

The first electrophilic Pd(II)-catalyzed allylic C-H alkylation is reported, providing a novel method for formation of sp3-sp3 C-C bonds directly from C-H bonds. A wide range of aromatic and heteroaromatic linear (E)-α-nitro-arylpent

Sequential hydrocarbon functionalization: Allylic C-H oxidation/vinylic C-H arylation

A Pd(II)/sulfoxide-catalyzed sequential allylic C-H oxidation/vinylic C-H arylation of α-olefins to furnish E-arylated allylic esters in high regio- and E:Z selectivities (>20:1) is reported. The broad scope of this method with respect to the α-olefin, ca

Macrolactonization via hydrocarbon oxidation

A novel Pd/sulfoxide-catalyzed macrolactonization reaction of linear ω-alkenoic acids is reported that proceeds via serial ligand-catalyzed allylic C-H oxidation. The scope of this macrolactonization appears to be very broad. Aryl, alkyl, and (Z)-α,β-unsaturated acids are all competent nucleophiles for this reaction, with the latter undergoing macrolactonization with no olefin isomerization. High functional group compatibility is observed that includes biologically and medicinally relevant functionality such as ortho-substituted salicylate esters, bis(indoyl)maleimides, and peptides. Evidence is provided to support the hypothesis that macrolactonization proceeds via inner-sphere functionalization from a templated π-allylPd carboxylate intermediate. Copyright

High-pressure Synthesis, Structure and Novel Photochemical Reactions of 7,7,8,8-Tetramethyl-7,8-disilabicycloocta-2,5-diene

7,7,8,8-Tetramethyl-7,8-disilabicycloocta-2,5-diene 1, prepared by the high-pressure reaction (10000 bar) of 1,1,2,2-tetramethyl-1,2-disilacyclohexa-3,5-diene and phenyl vinyl sulphoxide followed by elimination of benzenesulphenic acid, gave tetramethyldisilene (Me2Si=SiMe2) upon photolysis which underwent a photochemical reaction with benzene at 10 K in an argon matrix to regenerate the precursor.

Preparation and Nuclear Magnetic Resonance Studies of Pentacoordinated Phosphorus Compounds Containing Hexafluoroisopropoxy Groups

The reaction of 1,1,1,3,3,3-hexafluoroisopropyl benzenesulfenate (7) with tris(1,1,1,3,3,3-hexafluoroisopropyl)phosphite (8) yielded tetrakis(1,1,1,3,3,3-hexafluoroisopropoxy)(phenylthio)phosphorane (9).Variable-temperature 19F NMR studies of 9 show that