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Relevant academic research and scientific papers

Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes

The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

Visible light induced Trifluoromethyl Migration: Easy Access to α-Trifluoromethylated Ketones from Enol Triflates

Herein, we reported a novel method to synthesize α-trifluoromethylated ketones from enol triflates. Involving a cascade sulfur dioxide extrusion and a CF3 (trifluoromethyl) radical addition process, this reaction proceeds at room temperature an

Alpha-trifluoromethyl ketone compounds and preparation method thereof

The invention discloses a preparation method of alpha-trifluoromethyl ketone compounds and the compounds. A series of alpha-trifluoromethyl ketone compounds containing various functional groups are synthesized under conditions of room temperature and illumination. The preparation method of the alpha-trifluoromethyl ketone compounds and the compounds have the following advantages: operation is simple, raw materials are cheap and available, an application range of substrates is wide, most substrates are high in yield, and harsh reaction conditions are avoided.

Radical Desulfur-Fragmentation and Reconstruction of Enol Triflates: Facile Access to α-Trifluoromethyl Ketones

We report an efficient oxidative radical desulfur-fragmentation and reconstruction of enol triflates for the synthesis of α-CF3ketones. Preliminary mechanistic studies disclosed that oxidative fragmentation to release a CF3radical fr

METHOD FOR PRODUCING (2,2,2-TRIFLUOROETHYL)KETONE

PROBLEM TO BE SOLVED: To provide a method for efficiently producing (2,2,2-trifluoroethyl)ketone that is an important compound as a pharmaceutical fluorine-containing building block. SOLUTION: The method produces (2,2,2-trifluoroethyl)ketone represented by formula (3) by reacting 3-oxo-2-(trifluoromethyl)propanoic acid ester represented by formula (1) under the presence of an acid. (R1 is an alkyl group of C1 to 4; R2 is a C1 to 8 alkyl group, etc. substituted/un-substituted with F.) SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT

Activation of Trifluoromethylthio Moiety by Appending Iodonium Ylide under Copper Catalysis for Electrophilic Trifluoromethylation Reaction

A novel iodonium-ylide compound 2 that appends atrifluoromethylthio (SCF3) group is disclosed as a new, shelf-stable electrophilic trifluoromethylation reagent. Unlike known shelf-stable electrophilic trifluoromethylation reagents, 2 has a stable SCF3 group which is activated by appending iodonium ylide under copper catalysis via sulfonium ylide to generate a cationic trifluoromethyl (CF3) species. Reagent 2 was found to be an efficient electrophilic trifluoromethylation reagent for a wide range of silyl enol ethers 3 under copper catalysis. Cyclic and acyclic α-trifluoromethyl ketones 4 were obtained by reagent 2 in moderate to good yields. On the other hand, a difluoromethylthio analogue 5 did not affect intermolecular transfer difluoromethylation to substrates. Instead, intramolecular 1,4-migration proceeded similar to the Stevens rearrangement to provide 6 in 21% yield, independent of the presence of nucleophiles 3.

Fenton reagent-catalyzed trifluoromethylation of enamines of 3-oxocarboxylates with CF3I

The trifluoromethylation of enamines of ethyl 3-oxocarboxylates catalyzed by Fenton reagent with CF3I was investigated. Trifluoromethylation followed by acid hydrolysis provided 3-oxo-2-(trifluoromethyl)carboxylates in 64-94% yields, which were greater than those obtained by the trifluoromethylation of 3-oxocarboxylates as reported previously. Enamines trifluoromethylated at the 2-position were isolated as intermediates. Hydrolysis and successive decarboxylation of the obtained 3-oxo-2-(trifluoromethyl)carboxylates under acidic conditions provided (2,2,2-trifluoroethyl)ketones in satisfactory yields.

Carbene-Induced Intra- vs Intermolecular Transfer-Fluoromethylation of Aryl Fluoromethylthio Compounds under Rhodium Catalysis

The intra- vs intermolecular transfer-fluoromethylation of aryl fluoromethylthio compounds is proposed. Finely designed ArSCF3 (1a) nicely releases its trifluoromethyl (CF3) group intermolecularly under rhodium catalysis, whereas a difluoromethylated analogue, ArSCF2H compound 1b shows intramolecular reaction. (Chemical Presented).

Synthesis of α-trifluoromethyl ketones via the Cu-catalyzed trifluoromethylation of silyl enol ethers using an electrophilic trifluoromethylating agent

A method has been developed for the synthesis of α-trifluoromethyl ketones via the Cu-catalyzed trifluoromethylation of silyl enol ethers with an electrophilic trifluoromethylating agent, which produces a trifluoromethyl radical.

Copper-mediated trifluoromethylation of propiolic acids: Facile synthesis of α-trifluoromethyl ketones

Copper-mediated decarboxylative trifluoromethylation provides a new protocol for the efficient preparation of α-trifluoromethyl ketones from propiolic acids. It was found that water is involved as a reactant in the reaction, which is significantly different from the previously reported decarboxylative fluoroalkylation reactions.