426-58-4

Usage

Uses

Used in Organic Synthesis:
Phenyl (trifluoromethyl) sulfone is utilized as a reagent in organic synthesis, contributing to the creation of a variety of chemical compounds due to its unique structural features and reactivity.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Phenyl (trifluoromethyl) sulfone is employed as a precursor in the preparation of various pharmaceuticals. Its properties make it suitable for the development of new drugs with improved therapeutic profiles.
Used in Agrochemical Industry:
Phenyl (trifluoromethyl) sulfone also finds application in the agrochemical industry, where it serves as a starting material for the synthesis of agrochemicals, potentially enhancing crop protection and yield.
Used in Development of Fluorinated Compounds:
Due to its trifluoromethyl group, Phenyl (trifluoromethyl) sulfone has potential use as a prototype for developing new fluorinated compounds. These compounds may exhibit unique properties that can be harnessed in various chemical applications, including the creation of novel materials and advanced pharmaceutical agents.

Upstream product

• 456-56-4 phenyl trifluoromethylsulfide 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 71-43-2 benzene 
• 368-43-4 phenylsulfonyl fluoride 
• 754-25-6 trimethyl(trifluoromethyl)tin 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2314-97-8 iodotrifluoromethane 
• 618-41-7 Benzenesulfinic acid 
• 80-18-2 Methyl benzenesulfonate 
• 701-65-5 (trichloromethylthio)benzene 
• 16002-63-4 phenylmagnesium iodide 
• 100-58-3 phenylmagnesium bromide 
• 1961266-44-3 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate 
• 873-55-2 sodium benzenesulfonate 

Downstream Products

• 157246-90-7 (S)-4,5-dihydro-5-phenyl-1,3-dioxepin 
• 153867-09-5 2,2-Dimethyl-5-phenyl-4,5-dihydro-[1,3]dioxepine 
• 124244-39-9 (-)-(S)-2,5-dihydro-2-phenylfuran 
• 131516-05-7 (R)-2-phenyl-2,3-dihydrofuran 
• 16823-62-4 butyl phenyl sulfone 
• 599-70-2 ethyl phenyl sulfone 
• 6947-57-5 cyclohexyl phenyl sulfone 
• 3112-85-4 methylphenylsulfonate 
• 4238-09-9 phenyl isopropyl sulfone 
• 34009-05-7 (octane-1-sulfonyl)-benzene 
• 127-63-9 diphenyl sulphone 
• 16212-05-8 (allylsulfonyl)benzene 
• 384-37-2 1-nitro-2-(trifluoromethylsulfonyl)benzene 
• 1548-72-7 1-nitro-3-(trifluoromethylsulfonyl)benzene 

Relevant academic research and scientific papers

COMPOSITES, METHODS AND USES THEREOF

The present invention relates, in general terms, to methods of catalysing a reaction, including the steps of contacting a chemical entity comprising a sulphide moiety with a composite and an oxidant. The composite acts as a heterogeneous catalyst to oxidise the sulphide moiety. The present invention also relates to composites, methods of synthesising the composites and its use as a catalyst thereof.

Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes

Difunctionalization of strained cyclic alkynes presents a powerful strategy to build richly functionalized cyclic alkenes in an expedient fashion. Herein we disclose an efficient and flexible approach to achieve carbohalogenation, dicarbofunctionalization, aminohalogenation and aminocarbonation of readily available cyclohexenyl triflates. We have demonstrated the novel use of zincate base/nucleophile system for effective formation of key cyclohexyne intermediates and selective addition of various carbon and nitrogen nucleophiles. Importantly, leveraging the resulting organozincates enables the incorporation of a broad range of electrophilic partners to deliver structurally diverse cyclohexene motifs. The importance and utility of this method is also exemplified by the modularity of this approach and the ease in which even highly complex polycyclic scaffolds can be accessed in one step.

Rational Design and Development of Low-Price, Scalable, Shelf-Stable and Broadly Applicable Electrophilic Sulfonium Ylide-Based Trifluoromethylating Reagents

The development of two highly reactive electrophilic trifluoromethylating reagents (trifluoromethyl)(4-nitrophenyl)bis(carbomethoxy)methylide (1g) and (trifluoromethyl)(3-chlorophenyl)bis(carbomethoxy)methylide (1j) through structure-activity study was described. Under mild conditions, reagent 1g reacted with β-ketoesters and silyl enol ethers to give α-trifluoromethylated-β-ketoesters or α-trifluoromethylated ketones in high yields. In addition, reagent 1g could serve as a trifluoromethyl radical for a variety of trifluoromethylative transformations under visible light irradiation, including radical trifluoromethylation of electron-rich indoles and pyrroles and sodium aryl sulfinates as well as trifluoromethylative difunctionalization with styrene derivatives. On the other hand, as a complimentary, under reductive coupling conditions, reagent 1j reacted with a variety of (hetero)aryl iodides for the formation of trifluoromethylated (hetero)arenes.

One pot synthesis of trifluoromethyl aryl sulfoxides by trifluoromethylthiolation of arenes and subsequent oxidation with hydrogen peroxide

Hydrogen peroxide was used for oxidation of various aryl trifluoromethyl sulfides. Trifluoroacetic acid was used as an activating solvent that enables non-catalyzed oxidation and increases selectivity for sulfoxide formation. As shown by oxidation of thianthrene TFA enhances electrophilic character of the oxidant and further oxidation of sulfoxide group is blocked. We have joined trifluoromethylthiolation of arenes using a modified Billard reagent (p-ClPhNHSCF3) with oxidation of aryl trifluoromethyl sulfides using 1.2 equiv. of 30% aqueous hydrogen peroxide and this one-pot process has superior yields than would have been obtained in a two step process.

Trifluoroalkyl sulfone compound preparation method

The invention provides a trifluoroalkyl sulfone compound preparation method, which comprises: continuously feeding a trifluoroalkyl thioether compound, sodium tungstate dihydrate and a hydrogen peroxide solution into a continuous reactor through feeding equipment, and carrying out an oxidation reaction on the trifluoroalkyl thioether compound to obtain a product system containing the trifluoroalkyl sulfone compound, wherein the trifluoroalkyl thioether compound has a structure represented by a structural formula, R is any one selected from the following groups: linear alkyl, branched alkyl, substituted aryl, non-substituted aryl, substituted heterocyclic aryl, non-substituted heterocyclic aryl, non-substituted cyclic alkyl and substituted cyclic alkyl, and the temperature of the oxidationreaction is 25-50 DEG C. According to the invention, by using the continuous feeding, the material contact effect is improved, so that the thioether oxidation reaction can be carried out at a low temperature; and the oxidation reaction temperature is reduced to effectively reduce the decomposition of hydrogen peroxide and reduce the pressure resistance requirement on the continuous reactor.

Practical and efficient synthesis of aryl trifluoromethyl sulfones from arylsulfonyl chlorides with Umemoto's reagent II

A practical and efficient method for the synthesis of aryl trifluoromethyl sulfones has been developed by a tandem reaction of arylsulfonyl chlorides with Umemoto's reagent II. The advantageous features of this method are simple operation, mild reaction conditions, wide scope of substrates, high yield of products, and easy scalability.

Bifluoride Ion Mediated SuFEx Trifluoromethylation of Sulfonyl Fluorides and Iminosulfur Oxydifluorides

SuFEx is a new-generation click chemistry transformation that exploits the unique properties of S?F bonds and their ability to undergo near-perfect reactions with nucleophiles. We report here the first SuFEx-based procedure for the efficient synthesis of pharmaceutically important triflones and bis(trifluoromethyl)sulfur oxyimines from sulfonyl fluorides and iminosulfur oxydifluorides, respectively. The new process involves rapid S?F exchange with trifluoromethyltrimethylsilane (TMSCF3) upon activation by potassium bifluoride in anhydrous DMSO. The reaction tolerates a wide selection of substrates and proceeds under mild conditions without need for chromatographic purification. A tentative mechanism is proposed involving nucleophilic displacement of S?F by the trifluoromethyl anion via a five-coordinate intermediate. The utility of late-stage SuFEx trifluoromethylation is demonstrated through the synthesis and selective anticancer properties of a bis(trifluoromethyl)sulfur oxyimine.

Synthesis of Aryl Triflones through the Trifluoromethanesulfonylation of Benzynes

The direct synthesis of aryl triflones, that is, trifluoromethanesulfonyl arenes, was achieved through the trifluoromethanesulfonylation of benzynes. The trifluoromethanesulfonyl group, one of the fluorinated functional groups, is a highly electron-negative and mild lipophilic substituent. Aryl triflones have high potential in the synthesis of bioactive compounds and specialty materials. The treatment of 2-(trimethylsilyl)aryl trifluoromethanesulfonates with cesium fluoride in the presence of 15-crown-5 generated benzynes, which reacted with sodium trifluoromethanesulfinate followed by protonation with tBuOH under heating conditions, provided aryl triflones in moderated to good yields. Both symmetrical and unsymmetrical triflones were nicely accessed under the same reaction conditions. Interestingly, the trifluoromethanesulfonylation of unsymmetrical benzyne precursors proceeded smoothly to furnish corresponding aryl triflones in good yields with good to high regioselectivities. The balance of polarization of electric charge as well as steric hindrance of the benzyne intermediates are central factors to control the outcome of regioselectivity.

Ortho-lithiation reaction of aryl triflones

The ortho-lithiation of substituted arenes is a powerful methodology to synthesize ortho-substituted arenes. While a wide variety of directed metalation groups (DMGs) have been reported, trifluoromethyl sulfone has never been used. We disclose the first example of ortho-lithiation of aryl triflones. We found that the trifluoromethyl sulfonyl group is not only an important structural motif in biologically active molecules and specialty materials, but also an excellent DMG moiety for ortho-metalation reactions. The use of a base that causes steric hindrance, LTMP, is the key for successful transformation to furnish a variety of ortho-substituted aryl triflones in good yields. Further functionalization of resulting ortho-substituted aryl triflones was demonstrated by metal-catalyzed coupling reactions.

Copper-Mediated Di- and Monofluoromethanesulfonylation of Arenediazonium Tetrafluoroborates: Probing the Fluorine Effect

A copper-mediated di- and monofluoromethanesulfonylation of arenediazonium tetrafluoroborates using di- and monofluoromethanesulfinate reagents provides aryl difluoromethyl (or monofluoromethyl) sulfones in good yields. It was found that the relative reactivity of these sodium fluoroalkanesulfinates in the present reactions decreases in the following order: CH2FSO2Na > CF2HSO2Na > CF3SO2Na.