55059-13-7

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 67-68-5 dimethyl sulfoxide 
• 589-18-4 4-Methylbenzyl alcohol 
• 1779-54-0 methylthiomethyl(triphenyl)phosphonium chloride 
• 300396-83-2 1-(benzothiazol-2-ylthio)-2-(4-methylphenyl)ethene 
• 74-88-4 methyl iodide 
• 121194-40-9 1-((E)-2-Benzenesulfonyl-2-methylsulfanyl-vinyl)-4-methyl-benzene 

Relevant academic research and scientific papers

Method for preparing aryl vinyl alkyl thioether through C/C-S monatomic assembly process

The invention discloses a method for preparing aryl vinyl alkyl thioether through a C = C-S monatomic assembly process, which comprises the following steps: respectively providing an atom for a C = C-S structure by dimethyl sulfoxide, aromatic aldehyde ketone and sulfur-containing reagent sodium mercaptide/dithioether under the action of air atmosphere and alkali; the construction process is completed by one-pot reaction, and the product aryl vinyl alkyl thioether compound is obtained. The aryl vinyl of the aryl vinyl alkyl thioether compound prepared by the method comes from aromatic aldehyde ketone, but a double-bond carbon atom is added compared with the original aromatic aldehyde ketone raw material, and the method has the advantages of wide and easily available raw material source, environmental protection, low price, simple operation and facilitation of industrial production.

Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts

Phosphines were previously unusable as Pummerer-type nucleophiles due to competing redox chemistry with sulfoxides. Here we circumvent this problem to achieve a formal phosphine Pummerer reaction that offers thioalkyl phosphonium salts that, in turn, give rise to diverse vinyl sulfides via Wittig olefinations. Thirty vinyl sulfides are thus prepared from (alkylthioalkyl)triphenyl phosphonium salts and aldehydes. The hydrolysis of these vinyl sulfides offers an efficient and versatile two-step one-carbon homologation of aldehydes to ketones.

Cobalt modified N-doped carbon nanotubes for catalytic C=C bond formation via dehydrogenative coupling of benzyl alcohols and DMSO

The development of heterogeneous, cost-effective and environmentally benign catalysts to construct C=C bonds is highly desirable. We report here Co@N-doped carbon nanotubes (Co@NCNT) as a catalyst for a novel synthesis of styryl sulfides via dehydrogenative coupling of benzyl alcohols and DMSO under anaerobic conditions. This reaction maintains high atom efficiency as the C=C bond is formed without the cracking of the C-S bond. We proposed that Co modified N-doped carbon sites are the active sites, different from traditionally believed metal centers for dehydrogenative C-C coupling. Moreover, the Co@NCNT catalyst could be easily separated and recycled for at least six runs. This work opens up a new application of metal-N-C catalysts in C=C bond-forming reactions in synthetic chemistry.

The reactions of DMSO with arylaldehydes in the presence of sodium hydride

Dimethyl sulfoxide (DMSO) reacted with arylaldehydes under basic conditions to afford sulfide 1, β-(benzyloxy)styrene 2 and dialkyl sulfoxide 3, while the reaction of benzophenone with DMSO gave 1,1-diphenylethylene 4, 1,1-diphenyl-2-methylthioethylene 5 and sulfoxide 6 at the same time under the same conditions.

Mg-promoted stereoselective desulfonation of β-arylvinyl sulfone derivatives

β-Arylvinyl ρ-tolylsulfones, easily prepared from base-catalyzed condensation of aromatic aldehydes with a variety of ρ-tolylsulfones, were efficiently transformed to the corresponding (E)-β-substituted aromatic olefins in a stereoselective manner through Mg-promoted reduction. The reaction may be initiated through electron transfer from Mg metal to the vinyl sulfones to give the corresponding anionic species followed by stereoselective elimination of a sulfonyl group.

Desulfonylation of α-Methylthio-α,β-unsaturated Sulfones. A New Route to One Carbon Homologation of Aromatic Aldehydes

α-Methylthio-α,β-unsaturated sulfones 3 prepared from aromatic aldehydes 1 and sulfone 2 react with sodium hydrogen telluride in ethanol to undergo reductive desulfonylation to give vinyl sulfides 4 with certain extent of stereospecificity.A new route to one carbon homologation of aromatic aldehydes 1 to 5 is achieved by hydrolysis of 4 with titanium tetrachloride.

Reactions of (Benzothiazol-2-ylthio)(trimethylsilyl)methane. A General Method for α-Mercaptoalkylation by Alkylation and Alkylative Desilylation

Readily available (benzothiazol-2-ylthio)(trimethylsilyl)methane (2a) provides a convenient synthon for HSCH2- and enables the general conversions RR'CO -> RR'C(OH)CH(SH)R'' and RBr -> RCH(SH)SiMe3.The lithium derivative of 2a reacts with aldehydes and ketones to give Peterson olefination products which are protected vinyl mercaptans converted into vinyl mercaptans by reaction with methyllithium.This overall conversion is RR'CO -> RR'C:CHSH.