65325-65-7

Upstream product

• 123-09-1 4-chlorophenyl methyl sulfide 
• 107263-95-6 N-fluoropyridinium triflate 
• 107264-00-6 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate 
• 7205-90-5 chloromethyl 4-chlorophenyl sulfide 
• 373-53-5 fluoroiodomethane 
• 106-54-7 p-Chlorothiophenol 

Downstream Products

• 65325-69-1 1-chloro-4-((fluoromethyl)sulfinyl)benzene 

Relevant academic research and scientific papers

Optimized Monofluoromethylsulfonium Reagents for Fluoromethylene-Transfer Chemistry

An investigation of the properties and reactivity of fluoromethylsulfonium salts resulted in the redesign of the reagents for fluoromethylene transfer chemistry. The model reaction, fluorocyclopropanation of nitrostyrene, turned out to be a suitable platf

Direct and Chemoselective Electrophilic Monofluoromethylation of Heteroatoms (O-, S-, N-, P-, Se-) with Fluoroiodomethane

The commercially available fluoroiodomethane represents a valuable and effective electrophilic source for transferring the CH2F unit to a series of heteroatom-centered nucleophiles under mild basic conditions. The excellent manipulability offered by its liquid physical state (bp 53.4 °C) enables practical and straightforward one-step nucleophilic substitutions to retain the chiral information embodied, thus allowing it to overcome de facto the requirement for fluoromethylating agents with no immediate access. The high-yielding methodology was successfully applied to a variety of nucleophiles including a series of drugs currently in the market.

Fluorination of sulfides using IF5-Et3N-3HF

Mono- and difluorinations of sulfides were achieved using a novel fluorinating reagent, IF5-Et3N-3HF. The reagent is applicable for substrates having various electron-withdrawing groups, such as an ester, amide, ketone, ni

Bis(2-methoxyethyl)aminosulfur trifluoride: A new broad-spectrum deoxofluorinating agent with enhanced thermal stability

Bis(2-methoxyethyl)aminosulfur trifluoride, (CH3OCH2CH2)2NSF3 (Deoxo-Fluor reagent), is a new deoxofluorinating agent that is much more thermally stable than DAST (C2H5)2NSF3 and its congeners. It is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gem-difluorides, and carboxylic acids to the trifluoromethyl derivatives with, in some cases, superior performance compared to DAST. The enhanced stability is rationalized on the basis of conformational rigidity imposed by a coordination of the alkoxy groups with the electron-deficient sulfur atom of the trifluoride.

Facile synthesis of α-fluoroalkyl sulfides under the oxidative desulfurization-fluorination conditions

Upon treatment with n-Bu4NH2F3 and 1,3-dibromo-5,5- dimethylhydantoin, various organic sulfides underwent a Pummerer-type rearrangement, followed by fluorination, to give α-fluoro sulfides. The fluoro-Pummerer rearrangement, when applied to RCH(SMe)CF2SMe, gave trifluoro sulfides RCF(SMe)CF2SMe. When an HF-pyridine reagent was used as the fluorinating agent, an oxidative desulfurization-fluorination reaction occurred depending on the structure of the substrates.

Fluoro-Pummerer rearrangement under oxidative desulfurization fluorination conditions. Facile synthesis of oligofluoroalkyl sulfides

Upon treatment with n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin, various organic sulfides were readily fluorinated to give α-fluoro sulfides. When (HF)9-Py was used as the fluorinating agent, normal oxidative desulfurization fluorination occurred depending on the structure of the substrates.

Efficient Conversions of Thioethers to α-Fluoro Thioethers with DAST or DAST/Antimony(III) Chloride

Dialkyl or alkyl aryl thioethers, including nucleoside thioethers, undergo virtually quantitative conversion to α-fluoro thioethers with (diethylamino)sulfur trifluoride (DAST) in dichloromethane at ambient temperature.Antimony(III) chloride catalyzes the process.

Site-Selective Fluorination of Organic Compounds Using 1-Alkyl-4-fluoro-1,4-diazabicyclooctane Salts (Selectfluor Reagents)

The new "N-F"-type electrophilic reagent family of 1-alkyl-4-fluoro-1,4-diazabicyclooctane salts (derived from elemental fluorine (F2) and 1-alkyl-1,4-diazabicyclooctane salts) has been found to be very effective for the fluorination of a wide variety of organic substrates.These include steroidal enol acetates and silyl enol ethers, phenyl-substituted olefins, sulfides bearing α-H atoms, certain carbanions, and mildly activated aromatic compounds.The products were obtained with good yields and regioselectivity under very mild reaction conditions.

Method of fluorinating by using N-fluoropyridinium pyridine heptafluorodiborate

The present invention provides a novel compound represented as STR1 The present novel compound is prepared by reacting fluorine with pyridine-boron trifluoride and is useful as a fluorinating agent in the fluorination of organic compounds.

α-Fluorination of Sulfides with N-Fluoropyridinium Triflates

The reaction of sulfides possessing α-hydrogen with various N-fuoropyridinium salts was examined.While the fluorinating power increased in the order of N-fluoro-2,4,6-trimethylpyridinium triflate 12, and 3 no longer produced the α-fluoro sulfide.Triflate 1 was more reactive than the corresponding tetrafluoroborate 4.Thus, it was shown that 1 satisfactorily fluorinated various kinds of sulfides under very mild conditions, giving α-fluoro sulfides.A two-step mechanism, oxidative fluorination of sulfur and Pummerer-type rearrangement, was proposed for the fluorination.The corresponding α-fluoro sulfoxide or sulfones were easily prepared from the sulfides by successive fluorination-oxidation procedure.