39566-18-2

Upstream product

• 811-68-7 silver(I) trifluoromethanethiolate 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 55991-65-6 [1-(4-methoxyphenyl)vinyloxy]trimethylsilane 
• 2926-29-6 Langlois reagent 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 637-69-4 4-Methoxystyrene 
• 13422-77-0 3-(4-methoxy-phenyl)-3-oxo-propionic acid 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 1045821-71-3 N-[(trifluoromethyl)sulfanyl]aniline 
• 1443036-49-4 1-phenyl-2-(phenyl-λ³-iodaneylidene)-2-((trifluoromethyl)sulfonyl)ethan-1-one 

Relevant academic research and scientific papers

Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures

We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.

Triphosgene/Sodium Organosulfinate System: A General and Efficient Electrophilic Thiolation of Silylenol Ethers and Electron-Rich Heteroaromatics

An efficient and practical approach to electrophilic thiolation was developed by using commercially available triphosgene as a reductant and the appropriate alkyl- or arylsulfinates, which were transformed in situ into electrophilic RSCl intermediates in the presence of triphosgene. This procedure represents a general and powerful approach for the synthesis of α-(trifluoromethyl)thio-substituted ketones and thiolated electron-rich heteroaromatic compounds.

Synthesis and Use of Trifluoromethylthiolated Ketenimines

The synthesis of trifluoromethylthiolated ketenimines is herein described. They are easily synthesized from the corresponding α-trifluoromethylthiolated oximes upon activation with triflic anhydride and a base. The presumed nitrilium ion resulting from the Beckmann rearrangement is deprotonated to lead to the key intermediate, whose stability brought by the fluorinated substituent was unforeseeable. The reaction of these new building blocks with a variety of nucleophiles affords a vast array of cyclic and acyclic products bearing the valuable SCF3 moiety.

Ag(I)-Mediated Oxidative Radical Tri?fluoromethylthiolation of Alkenes

A simple, mild, and efficient method for an oxidative radical tri?fluoromethylthiolation of alkenes through AgSCF 3 /K 2 S 2 O 8 system has been developed. This reaction provides a straightforward way to synthesize a variety of useful α-SCF 3 -substituted ketone compounds from a wide range of alkenes in moderate to good yields.

Preparation method of alpha-trifluoromethylthio substituted acetophenone compound

The invention discloses a preparation method of an alpha-trifluoromethylthio substituted acetophenone compound. The preparation method comprises the following steps: by taking aryl ketone as a substrate, sodium trifluoromethanesulfinate as a trifluoromethylthio reagent, triphosgene as an additive, pyridine as a catalyst and dichloroethane as a solvent, in the nitrogen protection mode, stirring for12 hours at the temperature of 60 DEG C, performing a TLC tracking reaction, and conducting column chromatography isolation after sufficiently completing the reaction, thereby obtaining the alpha-trifluoromethylthio substituted acetophenone compound. According to the preparation method, the triphosgene is used as the reaction additive, so that using an expensive trifluoromethylthio reagent is avoided, but so far, a method for introducing trifluomethylthio has not been reported, the preparation method is simple and convenient, is low in cost, and is high in yield, a product is directly obtained, without any transition metal catalysis, and therefore, the preparation method is extremely high in practical popularization value.

Mechanistic Insights into the Decarboxylative Electrophilic Trifluoromethylthiolation of β-Ketocarboxylic Acids

A metal-free protocol for the domino trifluoromethylthiolation/decarboxylation of β-ketocarboxylic acids is described. The catalytic reactions take place in acetonitrile in the presence of aqueous ammonium hydroxide and N-trifluoromethylthiosaccharin. The sequence of events and reaction mechanism were established experimentally and using density functional theory calculations. This synthetic method offers a convenient alternative to known routes for the synthesis of α-trifluoromethylthio-substituted ketones.

An Unconventional Mechanistic Insight into SCF3 Formation from Difluorocarbene: Preparation of 18F-Labeled α-SCF3 Carbonyl Compounds

Trifluoromethylthiolation by sulfuration of difluorocarbene with elemental sulfur is described for the first time, which overrides long-standing trifluoromethyl anion-based theory. Mechanistic elucidation reveals an unprecedented chemical process for the

Synthesis of Trifluoromethylthiolated Alkenes and Ketones by Decarboxylative Functionalization of Cinnamic Acids

A tunable decarboxylative trifluoromethylthiolation of cinnamic acids with AgSCF3 was developed to afford trifluoromethylthiolated alkenes or ketones by using transition metal-mediated conditions.

Mild electrophilic trifluoromethylthiolation of ketones with trifluoromethanesulfanamide

A straightforward and convenient approach for trifluoromethylthiolation of various acyclic and cyclic ketones with PhNHSCF3 is described. The reaction proceeds smoothly in the presence of acetyl chloride at room temperature and affords α-trifluoromethylthiolated ketones in fair to good yields.

An efficient and practical approach to trifluoromethylthiolation of α-haloketones/α-haloarylmethanes

An efficient and practical approach to trifluoromethylthiolation of α-haloketones/α-haloarylmethanes was developed. The transformation employs only AgSCF3 and KI in situ generated active nucleophilic trifluoromethylthio species and cleanly occurs in up to quantitative yield at room temperature, thereby providing an unprecedentedly easy entry to various α-SCF3-substituted ketones/arylmethanes.