121194-35-2

Upstream product

• 82203-83-6 1-(p-methoxyphenyl)-3,3,3-trifluoropropyne 
• 680-15-9 2,2-difluoro-2-(fluorosulfonyl)acetate 
• 402578-95-4 dimethyl 1-(4-methoxyphenyl)-2-bromoethenyl phosphate 
• 111269-46-6 3-(Dimethyl-hydrazono)-1,1,1-trifluoro-3-(4-methoxy-phenyl)-propan-2-one 
• 123-75-1 pyrrolidine 
• 637-69-4 4-Methoxystyrene 
• 147531-11-1 trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 71-43-2 benzene 
• 2926-29-6 Langlois reagent 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 22390-98-3 1-(4-methoxyphenyl)ethenyl acetate 
• 887144-94-7 Togni's reagent II 

Downstream Products

• 59216-86-3 C₁₈H₁₆F₆O₂ 

Relevant academic research and scientific papers

Dual-gold(I)-generated trifluoromethylation of terminal alkynes with Togni's reagent

The interaction of a Au(I) catalyst (JohnPhosAu(I)-MeCN/SbF6) and the Togni's reagent 1, as a source of electrophilic trifluoromethyl group, has been studied in order to develop gold-catalysed alkyne trifluoromethylation reactions. Alkyne-CF3products were prepared in moderate yields (up to 46%) by electrophilic trifluoromethylation of terminal arylalkynes with Togni's reagent 1 in the presence of sub-stoichiometric amounts of gold catalyst (25%). The proposed addition-elimination reaction mechanism proceeds through a Au-Togni Reagent complex with a linear Togni Reagent-O-Au(I)-P-(phosphane) coordination mode (X-ray analysis). Alkyne deprotonation gives rapid formation of protonated Togni Reagent and a σ,π-acetylide dual-Au complex, confirmed by X-ray analysis. It was shown that the σ,π-dual-Au complex activates for trifluoromethylation, most likely by transfer of a [LAu]+fragment to the alkyne substrate. The resulting reactive π-Au+-alkyne intermediate probably undergoes O-/CF3-addition of Togni Reagent, and final elimination of Togni alcohol gives the alkyne-CF3product.

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.

Electrochemical Synthesis of Fluorinated Ketones from Enol Acetates and Sodium Perfluoroalkyl Sulfinates

The electrochemical synthesis of fluorinated ketones from enol acetates and RfSO2Na in an undivided cell under constant current conditions was developed. The electrosynthesis proceeded via perfluoroalkyl radical generation from sodium perfluoroalkyl sulfinate followed by addition to the enol acetate and transformation of the resulting C radical to a fluorinated ketone. The method is applicable to a wide range of enol acetates and results in the desired products in yields of 20 to 85%.

One-Pot Synthesis of CF3-Substituted Vinyl Trifluoromethanesulfonamides from Imines and Trifluoromethanesulfonic Anhydride

The one-pot triflation/radical trifluoromethylation/triflation of imines leading to CF3-substituted vinyl trifluoromethanesulfonamides is described. The reaction proceeds via the radical trifluoromethylation of vinyl trifluoromethanesulfonamides as the key step. This reaction is suitable for a variety of imines that contain halogen atoms, electron-donating groups, or electron-withdrawing groups, leading to moderate to good yields. Vinyl trifluoromethanesulfonamides can act as bifunctional reagents whereby they serve as both the trifluoromethyl radical source and the radical acceptor.

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.

A Concise and Efficient Approach to 2,6-Disubstituted 4-Fluoro pyrimidines from α-CF 3 Aryl Ketones

Herein, a concise and efficient protocol to synthesize a series of 2,6-disubstituted 4-fluoropyrimidines as universal and useful building blocks in medicinal chemistry is reported. From readily accessible α-CF 3 aryl ketones and different amidine hydrochlorides, this method provides a very practical approach to this kind of compounds under mild conditions with good to excellent yields.

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.

METHOD FOR PRODUCING IMINES CONTAINING FLUOROALKYL GROUP

PROBLEM TO BE SOLVED: To provide a method for producing more inexpensive and versatile α-fluoroalkyl ketone compound and β-fluoroalkyl amine compound. SOLUTION: The α-fluoroalkyl ketone compound or β-fluoroalkyl amine compound are produced by treating N-f

On the reactivity of anodically generated trifluoromethyl radicals toward aryl alkynes in organic/aqueous media

An in-depth study of the reaction of electrochemically generated trifluoromethyl radicals with aryl alkynes in the presence of water is presented. The radicals are readily generated by anodic oxidation of sodium triflinate, an inexpensive and readily avai

Photoredox generation of the trifluoromethyl radical from borate complexes: Via single electron reduction

A method for the generation of the CF3 radical from CF3-substituted borate complexes bearing a pyridine-N-oxide ligand is described. Cleavage of the C-B bond occurs via single electron reduction by a Cu(i) photocatalyst activated by visible light.