127138-66-3

Upstream product

• 75-18-3 dimethylsulfide 
• 2923-28-6 silver trifluoromethanesulfonate 
• 100-39-0 benzyl bromide 
• 766-92-7 [(methylthio)methyl]-benzene 
• 333-27-7 methyl trifluoromethanesulfonate 
• 100-52-7 benzaldehyde 

Downstream Products

• 1027755-00-5 trans,trans-5,17-bis(3'-phenyl-2'-oxiranyl)-25,26,27,28-tetrapropoxycalix[4]arene 
• 2308-20-5 4-methoxyphenyl 2-phenylacetate 
• 834-14-0 p-benzylanizole 

Relevant academic research and scientific papers

Redox-Neutral Borylation of Aryl Sulfonium Salts via C-S Activation Enabled by Light

Reported here is a novel photoinduced strategy for the borylation of aryl sulfonium salts using bis(pinacolato)diboron as the boron source. This method exploits redox-neutral aryl sulfoniums to gain access to aryl radicals via C-S bond activation upon photoexcitation under transition-metal-free conditions. Therefore, it grants access to diverse arylboronate esters with good performance from easily available aryl sulfoniums accompanied by mild conditions, operational simplicity, and easy scalability.

Nickel-Catalyzed Reductive Cross-Coupling of Benzylic Sulfonium Salts with Aryl Iodides

A nickel-catalyzed cross-electrophile coupling of benzylic sulfonium salts with aryl iodides has been developed, providing direct access to diarylalkanes from readily available and stable coupling partners. Preliminary mechanistic studies suggest that the C-S bond cleavage proceeds through a single-electron transfer process to generate a benzylic radical.

Nickel-Catalyzed Negishi-Type Arylation of Trialkylsulfonium Salts

Negishi-type arylation of trialkylsulfonium salts with arylzinc reagents has been accomplished under nickel catalysis. The use of cyclohexanethiol as an additional ligand was found to be particularly important to promote C-S cleavage. The present reaction accommodates one-pot arylation of dialkyl sulfides by combining with S -methylation with MeOTf. Mechanistic experiments suggest that C-S cleavage would proceed via single-electron transfer (SET) to generate the most stable carbon-centered radical and that the thiolate ligand would promote the C-S cleavage and radical recombination step.

Palladium-Catalyzed Alkoxycarbonylation of Arylsulfoniums

Alkoxycarbonylation of arylsulfoniums has been developed with the aid of a catalytic amount of a palladium-Xantphos complex under an atmospheric pressure of CO gas. Various functional groups such as carbonyl, cyano, halo, and sulfonyl groups were well tolerated under the present catalysis. Since aryldimethylsulfoniums were readily prepared from the corresponding aryl methyl sulfides and methyl triflate, one-pot alkoxycarbonylation of aryl methyl sulfides could be accomplished.

Novel chiral calix[4]arenes by direct asymmetric epoxidation reaction

(Chemical Equation Presented) We report the first asymmetric synthesis of trans optically active (+) C2 1,3-bisarylepoxide of calix[4]arene in excellent chemical yield and >99% ee, and its enantiospecific conversion to the corresponding bis-dio