121194-36-3

Upstream product

• 82203-84-7 1-(4-chlorophenyl)-3,3,3-trifluoro-1-propyne 
• 121194-28-3 [(E)-1-(4-Chloro-phenyl)-3,3,3-trifluoro-propenyl]-methyl-diazene 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 58518-76-6 ((1-(4-chlorophenyl)vinyl)oxy)trimethylsilane 
• 680-15-9 2,2-difluoro-2-(fluorosulfonyl)acetate 
• 39646-27-0 dimethyl 1-(4-chlorophenyl)-2-bromoethenyl phosphate 
• 138616-25-8 (E)-p-chlorobenzaldehyde N,N-dimethylhydrazone 
• 111269-42-2 3-(4-Chloro-phenyl)-3-(dimethyl-hydrazono)-1,1,1-trifluoro-propan-2-one 
• 123-75-1 pyrrolidine 
• 1073-67-2 4-vinylbenzyl chloride 
• 147531-11-1 trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt 
• 104-88-1 4-chlorobenzaldehyde 
• 2314-97-8 iodotrifluoromethane 
• 1280738-14-8 [1-(4-chlorophenyl)vinyloxy]triisopropylsilane 

Relevant academic research and scientific papers

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.

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%.

Scissoring Enaminone C=C Double Bond by Free Radical Process for the Synthesis of α-Trifluoromethyl Ketones with CF3SO2Na

The C=C double bond cleavage on tertiary enaminones, enabling the formation of a new C-CF3 bond, has been realized as a practical method for the synthesis of α-trifluoromethyl ketones with only the promotion of TBHP and ambient heating. Control experiments support that the reactions proceed via a featured free radical process. The deuterium labeling experiment employing D2O indicates that water participated in the product formation by donating the hydrogen atom for the newly generated α-C-H bond in the product.

METHOD FOR PRODUCING α-FLUOROALKYL KETONE AND β-FLUOROALKYL ALCOHOL

PROBLEM TO BE SOLVED: To provide a method for producing α-fluoroalkyl ketone and β-fluoroalkyl alcohol conveniently, inexpensively and efficiently. SOLUTION: A method for producing α-fluoroalkyl ketone represented by formula (II) (where Rf is a fluoroalkyl group) includes reacting an alkyne compound represented by formula (I) (where R1 is a chain hydrocarbon group, cyclic aliphatic hydrocarbon group, aromatic hydrocarbon group, heterocyclic group, -OR3, -NR4R4', R2 is a hydrogen atom, trialkylsilyl group, diallyl alkylsilyl group, or triallylsilyl group), in the presence of a radical initiator, with a fluoroalkyl sulfonic acid. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

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.

Direct Photoassisted α-Trifluoromethylation of Aromatic Ketones with Trifluoroacetic Anhydride (TFAA)

Direct α-Trifluoromethylation of acetophenone derivatives was achieved by using trifluoroacetic anhydride (TFAA) as the trifluoromethyl source and pyridine-N-oxide (Py?O) as activator and oxidant under visible light irradiation and tris-(2,2′-bipyridine)ruthenium(II) hexafluorophosphate (Ru(bpy)3(PF6)2) as the photocatalyst. Different acetophenone derivatives could be converted to the corresponding α-CF3 derivatives with high selectivity. Extensive mechanistic investigation revealed the formation of vinyl trifluoroacetate as the key intermediate for this transformation. (Figure presented.).

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

Photooxidative Keto-Trifluoromethylation of Styrenes by Means of an Anthraquinone-Based Organocatalyst

α-Trifluoromethyl ketones are versatile building blocks for the synthesis of various trifluoromethyl-functionalized molecules. Although there are significant advantages in the development of methods toward direct transformations of styrenes into α-trifluoromethyl ketones, most procedures leading to α-trifluoromethyl ketones require heavy- or transition-metal-based complexes. Herein, a novel method is developed for the synthesis of α-trifluoromethyl ketones via anthraquinone-catalyzed photooxidative keto-trifluoromethylation of styrenes with the readily available Langlois reagent (CF 3 SO 2 Na) under an oxygen atmosphere. The reactions proceed smoothly to give the products in moderate to excellent yield with good selectivity.

Organosilicon Reducing Reagents for Stereoselective Formations of Silyl Enol Ethers from α-Halo Carbonyl Compounds

Salt-free stereoselective synthesis of silyl enol ethers was achieved by treating α-halo carbonyl compounds with 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-dihydropyrazine. In this reaction, easily removable trimethylsilyl halides and 2,3,5,6-tetramethylpyrazine were generated as the reaction byproducts. Due to the inertness of the reaction byproducts, we found a one-pot transformation of the in situ generated silyl enol ethers into various α-functionalized carbonyls by reaction with Togni-II reagent or aldehydes.

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.