130654-91-0

Upstream product

• 130654-80-7 1-methoxy-2-(3,3,3-trifluoroprop-1-yn-1-yl)benzene 
• 135339-88-7 ((1-(2-methoxyphenyl)vinyl)oxy)trimethylsilane 
• 767-91-9 1-ethynyl-2-methoxybenzene 
• 105273-33-4 1-chloro-2-(trimethylsilylethynyl)benzene 
• 615-41-8 2-iodochlorobenzene 
• 612-15-7 o-methoxystyrene 
• 1073483-49-4 1-(1-azidovinyl)-2-methoxybenzene 
• 2926-29-6 Langlois reagent 
• 887144-94-7 Togni's reagent II 
• 7342-00-9 3-(2-methoxyphenyl)prop-2-ynoic acid 
• 529-28-2 4-iodoanisol 

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.

Photoredox-catalysed redox-neutral trifluoromethylation of vinyl azides for the synthesis of α-trifluoromethylated ketones

A redox-neutral, mild, and simple protocol is developed for the synthesis of α-trifluoromethylated ketones from vinyl azides under transition-metal-free conditions. In the presence of organic photoredox catalyst N-methyl-9-mesityl acridinium and sodium trifluoromethanesulfinate, a broad range of substituted vinyl azides were found to react smoothly upon visible-light irradiation, readily furnishing the corresponding products in satisfied yields.

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).

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.

Preparation of 1-Aryl- or 1-Alkenyl-2-(perfluoroalkyl)acetylenes

1-Aryl- or 1-alkenyl-2-(perfluoroalkyl)acetylenes were produced in high yields by coupling reaction of aryl or alkenyl iodides with (perfluoroalkynyl)zinc compounds prepared from the corresponding (perfluoroalkyl)acetylenes in the presence of Pd catalyst.