60375-88-4

Upstream product

• 97571-11-4 (trifluoromethyl)cadmiumbromide 
• 4392-24-9 Cinnamyl bromide 
• 353-83-3 1,1,1-trifluoro-2-iodoethane 
• 66680-87-3 (E)-1-phenyl-(2-tributylstannyl)ethene 
• 66680-87-3 (Z)-tributyl(styryl)stannane 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 300-57-2 allylbenzene 
• 887144-94-7 Togni's reagent II 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 104-54-1 3-Phenylpropenol 
• 536-74-3 phenylacetylene 
• 100-42-5 styrene 
• 1895006-01-5 dimesityl(trifluoromethyl)sulfonium trifluoromethanesulfonate 

Relevant academic research and scientific papers

Trifluoroethylation of Alkynes: Synthesis of Allylic-CF3 Compounds by Visible-Light Photocatalysis

Two types of allylic trifluoromethylated compounds were synthesized by reacting alkynes with CF3CH2I using visible-light photocatalysis. Subtle differences in the catalytic system controlled the selectivity of iodotrifluoroethylation

Dehydrative Ring-Opening of gem-Difluorocyclopropyl Carbinols to Allylic Trifluoromethyl and Difluorohalomethyl Derivatives Promated by Titanium Tetrahalide

We report herein the titanium tetrahalide-promoted dehydrative ring-opening of gem-difluorocyclopropyl carbinols as a novel method for the synthesis of (E)-allylic CF3, (E)-allylic CF2Cl, and (E)-allylic CF2Br compounds. This TiF4-promoted reaction appears to proceed via a concerted SN2' mechanism. A control experiment revealed that the TiCl4-promoted ring-opening initially proceeds by conversion of the gem-difluorocyclopropyl carbinol into a gem-difluorocyclopropyl chloride intermediate.

Photocatalytic Palladium-Catalyzed Fluoroalkylation of Styrene Derivatives

A visible light induced palladium-catalyzed fluoroalkylation method was developed. The Heck-type alkyl coupling reaction enables the introduction of trifluoroethyl, difluoroethyl and other fluoroalkyl fragment into styrenes under mild reaction conditions without the use of additional photosensitizers and ensures access to fluoroalkylated olefins on a broad scale.

Copper-Catalyzed Oxidative Trifluoromethylation of Terminal Alkenes Using AgCF3

A mild and convenient reaction for oxidative trifluoromethylation of terminal alkenes was developed using in situ generated AgCF3 in the presence of a copper catalyst. The reaction proceeded under an air atmosphere to afford trifluoromethylated allylic compounds in moderate to good yield. This reaction, with no need for highly hygroscopic or corrosive reagents, features not only a simple operation but also various functional group tolerances.

Copper-Catalyzed Trifluoromethylation of Alkyl Bromides

Copper oxidative addition into organohalides is a challenging two-electron process. In contrast, formal oxidative addition of copper to C sp2 carbon-bromine bonds can be accomplished by employing latent silyl radicals under photoredox conditions. This novel paradigm for copper oxidative addition has now been applied to a Cu-catalyzed cross-coupling of C sp3-bromides. Specifically, a copper/photoredox dual catalytic system for the coupling of alkyl bromides with trifluoromethyl groups is presented. This operationally simple and robust protocol successfully converts a variety of alkyl, allyl, benzyl, and heterobenzyl bromides into the corresponding alkyl trifluoromethanes.

Catalytic One-Step Deoxytrifluoromethylation of Alcohols

A new bench-stable trifluoromethylation reagent, phenyl bromodifluoroacetate, converts readily available alcohols to trifluoromethanes in a Cu-catalyzed deoxytrifluoromethylation reaction. This reaction streamlines access to target biologically active molecules, and should be useful for a variety of medicinal, agricultural, and materials chemists.

Copper-catalyzed decarboxylative trifluoroethylation of cinnamic acids

An efficient Cu-catalyzed stereoselective trifluoroethylation through the decarboxylative cross-coupling of cinnamic acid derivatives with CF3CH2I is described. The ready availability of the starting materials, the high level of functional group tolerance, and excellent E selectivity make this protocol a safe and operationally convenient strategy for the efficient synthesis of trifluoroethyl derivatives.

Copper(I)-mediated direct trifluoromethylthiolation of allylic halides with elemental sulfur and (trifluoromethyl)trimethylsilane

Abstract A new method has been developed for the copper-mediated trifluoromethylthiolation of allylic halides by using potassium fluoride, elemental sulfur, and (trifluoromethyl)trimethylsilane in anhydrous N,N-dimethylformamide. This protocol provides facile access to a variety of allylic trifluoromethyl thioethers in moderate to good yields under mild, ligand-free reaction conditions.

Copper-catalyzed decarboxylative trifluoromethylation of allylic bromodifluoroacetates

The development of new synthetic fluorination reactions has important implications in medicinal, agricultural, and materials chemistries. Given the prevalence and accessibility of alcohols, methods to convert alcohols to trifluoromethanes are desirable. However, this transformation typically requires four-step processes, specialty chemicals, and/or stoichiometric metals to access the trifluoromethyl-containing product. A two-step copper-catalyzed decarboxylative protocol for converting allylic alcohols to trifluoromethanes is reported. Preliminary mechanistic studies distinguish this reaction from previously reported Cu-mediated reactions.

Regio- and stereoselective allylic trifluoromethylation and fluorination using CuCF3 and CuF reagents

Copper-mediated trifluoromethylation of allylic chlorides and trifluoroacetates was performed using a convenient Cu-CF3 reagent. The reaction is suitable for selective synthesis of allyl trifluoromethyl species. Mechanistic studies indicate that the reaction proceeds via a nucleophilic substitution mechanism involving allyl copper intermediates. The analogous Cu-F reagent was suitable for fluorination of allyl chlorides. Stereodefined cyclic substrates reacted regio- and stereoselectively.