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Upstream product

• 622-97-9 1-ethenyl-4-methylbenzene 
• 353-83-3 1,1,1-trifluoro-2-iodoethane 
• 766-97-2 4-n-methylphenylacetylene 
• 22390-99-4 4'-methylacetophenon enol acetate 
• 66616-85-1 α-(4-methylphenyl)acrylic acid 
• 104-87-0 4-methyl-benzaldehyde 
• 2314-97-8 iodotrifluoromethane 
• 132589-36-7 1-(4-methylphenyl)prop-2-yn-1-ol 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 887144-94-7 Togni's reagent II 
• 40122-37-0 1-(p-tolyl)cyclopropan-1-ol 
• 692-51-3 (E)-trimethyl(3,3,3-trifluoroprop-1-en-1-yl)silane 
• 122-00-9 para-methylacetophenone 
• 19832-78-1 1-(4-methylphenyl)prop-2-en-1-one 

Relevant academic research and scientific papers

Iron-Catalyzed Oxyalkylation of Terminal Alkynes with Alkyl Iodides

A general oxyalkylation of terminal alkynes enabled by iron catalysis has been developed. Primary and secondary alkyl iodides acted as the alkylating reagents and afforded a range of α-alkylated ketones under mild reaction conditions. Acetyl tert-butyl peroxide (TBPA) was used as the radical relay precursor, providing the initiated methyl radical to start the radical relay process. Preliminary mechanistic studies were conducted, and late-stage functionalizations of natural product derivatives were performed.

Base-Promoted Double-Bond-Migration/Hydrolysis/Isomerization of 4-Aryl-1,1,1-trifluorobut-2-en-2-yl Trifluoromethanesulfonates: A Metal-Free Approach to β-Trifluoromethyl Ketones

A method for the synthesis of β-trifluoromethyl ketones promoted by a base is described. In the presence of DBU, 1-aryl-4,4,4-trifluoromethylbutanones with various functional groups were obtained through the reaction of 4-aryl-1,1,1-trifluorobut-2-en-2-yl

Synthesis of β-CF 3 Ketones through Copper/Silver Cocatalyzed Oxidative Coupling of Enol Acetates with ICH 2 CF 3

A simple method for the synthesis of β-CF 3 ketones through copper/silver cocatalyzed oxidative coupling of enol acetates with ICH 2 CF 3 has been developed. Enol acetates were chosen as the source of carbonyl group, giving the β-CF 3 ketones in moderate yields. Control experiments imply that a radical process maybe involved in this reaction.

Free-Radical-Promoted Copper-Catalyzed Decarboxylative Alkylation of α,β-Unsaturated Carboxylic Acids with ICH2CF3 and Its Analogues

A novel and efficient free-radical-promoted copper-catalyzed decarboxylative alkylation of α,β-unsaturated carboxylic acids with ICH2CF3 and its analogues has been developed. This methodology provides a convenient access to the synthesis of allylic trifluoromethyl and β-CF3 ketone containing compounds as well as other biologically useful fluorinated molecules and materials.

Copper/Silver Cocatalyzed Oxidative Coupling of Vinylarenes with ICH2CF3 or ICH2CHF2 Leading to β-CF3/CHF2-Substituted Ketones

A novel copper/silver cocatalyzed oxidative coupling of vinylarenes with ICH2CF3 or ICH2CHF2 through a radical process has been developed. The transformation provides an attractive approach to β-CF3/CHF2-substituted ketones, with the advantages of easily available starting materials and operational simplicity.

Copper-catalysed ring-opening trifluoromethylation of cyclopropanols

A copper-catalysed ring-opening trifluoromethylation reaction of cyclopropanols has been developed. Various β-trifluoromethyl ketones are obtained in good to excellent yields under mild reaction conditions. The present method also exhibits good functional-group compatibility. The mechanism of this new ring-opening trifluoromethylation reaction was investigated by radical trapping reactions.

Synthesis of β-Trifluoromethylated Ketones from Propargylic Alcohols by Visible Light Photoredox Catalysis

Regioselective trifluoromethylation at a remote position represents an important challenge in the development of biologically active molecules and functional materials. A practical method to access β-trifluoromethyl ketones from readily available propargylic alcohols by visible light photocatalysis has been developed. Trifluoromethylation of propargylic alcohols with CF3I in the presence of Ru(bpy)3Cl2 as the photocatalyst followed by double-bond migration/keto-enol tautomerization provides β-trifluoromethyl ketones as the final product. β-Trifluoromethyl ketones are synthesized from readily available propargylic alcohols by visible light photocatalysis. Trifluoromethylation followed by double-bond migration/keto-enol tautomerization provides β-trifluoromethyl ketones as the final product.

Boron-trihalide-promoted regioselective ring-opening reactions of gem-difluorocyclopropyl ketones

Boron trihalide-promoted ring-opening reactions of gem-difluorocyclopropyl ketones to give the corresponding β-trifluoromethyl ketones and β-halodifluoromethyl ketones were described. It was found that boron trihalides act as both Lewis acids and nucleophiles and the proximal bond prefers to cleave in this transformation.

Oxidative 3,3,3-trifluoropropylation of arylaldehydes

A reaction between (E)-trimethyl(3,3,3-trifluoroprop-1-en-1-yl)silane (1) and arylaldehydes 2 was triggered by fluoride anions to afford aryl 3,3,3-trifluoropropyl ketones 3 in moderate to good yield. A mechanistic study of this reaction indicated that it occurred via an allyl alkoxide (4). A subsequent 1,3-proton shift of the benzylic proton of 4 forms 3. This reaction involves oxidative 3,3,3-trifluoropropylation of an arylaldehyde to afford 4,4,4-trifluoro-1-arylbutan-1-one.

A facile parallel synthesis of trifluoroethyl-substituted alkynes

Trifluoroethylation made easy: The ease of execution of the reaction (see scheme), which runs under mild conditions and without the need for additional base or ligands, allows for the rapid parallel synthesis of a broad variety of trifluoroethylated alkynes. Both experimental and theoretical analyses indicate that the trifluoromethylcarbene could undergo concerted insertion into the Csp-H bond of the alkyne. Copyright