438-24-4

Upstream product

• 75-63-8 Bromotrifluoromethane 
• 529-20-4 2-methylphenyl aldehyde 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 341-39-9 2-methyl-α,α,α-trifluoroacetophenone 
• 95-46-5 2-methylphenyl bromide 
• 97-72-3 2-Methylpropionic anhydride 
• 615-37-2 ortho-methylphenyl iodide 
• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 
• 421-53-4 2,2,2-trifluoro-1,1-ethanediol 
• 932-31-0 ortho-tolylmagnesium bromide 
• 75-46-7 trifluoromethan 

Downstream Products

• 1682-47-9 2,2,2-Trifluor-1-o-tolyl-1-(4-chlor-phenyl)-aethan 
• 158884-39-0 2,2,2-trifluoro-1-[2-(methyl)phenyl]ethyl 4-methylbenzenesulfonate 
• 158884-40-3 1-Methyl-2-(2,2,2-trifluoroethyl)benzene 
• 158884-42-5 2-(2,2,2-Trifluoroethyl)benzaldehyde 
• 158884-41-4 1-(Bromomethyl)-2-(2,2,2-trifluoroethyl)benzene 
• 158884-11-8 <2-(2,2,2-Trifluoroethyl)phenyl>diazomethane 
• 158884-12-9 C₉H₆⁽²⁾HF₃N₂ 
• 158884-43-6 2-(2,2,2-Trifluoroethyl)benzaldehyde tosylhydrazone 
• 1135312-19-4 2,2,2-trifluoro-1-(2'-methylphenyl)ethyl isobutyrate 
• 1135311-82-8 (S)-2,2,2-trifluoro-1-(2'-methylphenyl)ethyl isobutyrate 
• 131832-01-4 (R)-2,2,2-trifluoro-1-(2'-methylphenyl)ethanol 
• 438-24-4 (S)-2,2,2-trifluoro-1-(2'-methylphenyl)ethanol 
• 341-39-9 2-methyl-α,α,α-trifluoroacetophenone 

Relevant academic research and scientific papers

Synthesis of Unsymmetric Triarylmethanes Bearing CF 3-Substituted All-Carbon Quaternary Stereocenters: 1,6-Arylation of δ-Trifluo romethyl Substituted para -Quinone Methides

Pre-synthesized δ-CF 3-δ-aryl-disubstituted para -quinone methides bearing δ-substituents were identified as isolable and storable substrates for 1,6-arylation reactions. A broad range of electron-rich arenes and heteroarenes participated in the arylation process, furnishing a wide array of unsymmetrical CF 3-substituted triarylmethanes in high efficiency. The mild and expeditious protocol exhibited broad scopes of both arene and para -quinone methide components.

One-Pot Successive Turbo Grignard Reactions for the Facile Synthesis of α-Aryl-α-Trifluoromethyl Alcohols

A novel straightforward one-pot methodology for two successive turbo Grignard reagent (iPrMgCl·LiCl) reactions, was developed for a facile synthesis of α-aryl-α-trifluoromethyl alcohols, motifs of value in pharmaceutical chemistry. The method displayed broad functional group tolerance, including reducible groups. Dual roles of iPrMgCl·LiCl were exploited in the tandem reaction with commercially available iodoarenes or iodoheteroarenes and 2,2,2-trifluoroethyl trifluoroacetate. The process encompasses three successive reactions in a one-pot process: the iPrMgCl·LiCl-mediated iodine/magnesium-exchange reaction of iodoarenes or iodoheteroarenes; nucleophilic addition of various generated aryl or heteroarylmagnesium reagents to 2,2,2-trifluoroethyl trifluoroacetate; and the reduction of in-situ generated aryl trifluoromethyl ketones with iPrMgCl·LiCl, to produce the corresponding α-aryl or α-heteroaryl-α-trifluoromethyl alcohols bearing various substituents, including reducible functional groups in good to excellent yields.

Gas/Liquid-Phase Micro-Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N-Sulfinylimines

A micro-flow nucleophilic trifluoromethylation of carbonyl compounds using gaseous fluoroform was developed. This method also allows the first micro-flow transformation of N-sulfinylimines into trifluoromethyl amines with excellent diastereoselectivity. To demonstrate the synthetic utility of this micro-flow synthesis, the formal micro-flow synthesis of Efavirenz is described.

Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling of Secondary α-(Trifluoromethyl)benzyl Tosylates

A palladium-catalyzed C(sp3)?C(sp2) Suzuki–Miyaura cross-coupling of aryl boronic acids and α-(trifluoromethyl)benzyl tosylates is reported. A readily available, air-stable palladium catalyst was employed to access a wide range of functionalized 1,1-diaryl-2,2,2-trifluoroethanes. Enantioenriched α-(trifluoromethyl)benzyl tosylates were found to undergo cross-coupling to give the corresponding enantioenriched cross-coupled products with an overall inversion in configuration. The crucial role of the CF3 group in promoting this transformation is demonstrated by comparison with non-fluorinated derivatives.

Catalytic highly enantioselective transfer hydrogenation of β-trifluoromethyl nitroalkenes. An easy and general entry to optically active β-trifluoromethyl amines

In the presence of a thiourea catalyst, β-CF3 nitroalkenes react with Hantzsch esters in a highly enantioselective fashion, giving a broad range of β-CF3 amine precursors with a tertiary stereocentre at the β-position. This reaction

Synthesis of Perfluoroalkyl-Substituted Vinylcyclopropanes by Way of Enhanced Neighboring Group Participation

A simple, high yielding, two-step, one-pot protocol for the preparation of trifluoromethyl-substituted vinylcyclopropanes from α-CF3 homoallyl alcohols is disclosed. Destabilization of the cationic intermediate by the electron-withdrawing CF3 group greatly enhances neighboring group participation of the alkene, allowing ring closure to predominate. The reaction can be extended to the difluoromethyl and pentafluoroethyl group, enabling the preparation of a diverse array of fluoroalkyl-substituted vinylcyclopropanes. A diverse array of fluoroalkyl-substituted vinylcyclopropanes are prepared in a simple, high-yielding, two-step, one-pot protocol by means of cationic ring-closure.

Nucleophilic trifluoromethylation of carbonyl compounds: Trifluoroacetaldehyde hydrate as a trifluoromethyl source

A feasible nucleophilic trifluoromethylating protocol has been developed using trifluoroacetaldehyde hydrate as an atom-economical trifluoromethyl source. The reaction was found to be applicable to the nucleophilic trifluoromethylation of a broad spectrum of carbonyl compounds with satisfactory yields in general. DFT calculations have been performed to provide mechanistic insight into the present and related reactions employing 2,2,2-trifluoro-1- methoxyethanol and hexafluoroacetone hydrate.

Nonenzymatic kinetic resolution of racemic 2,2,2-trifluoro-1-aryl ethanol via enantioselective acylation

Kinetic resolution of a series of 2,2,2-trifluoro-1-aryl ethanol with (R)-benzotetramisole as the catalyst has been investigated. The result showed that when the aryl group in the substrate was a phenyl (or a phenyl substituted by an electron-donating group) or a naphthyl (an extended phenyl) group, the system could give an s value higher than 20. Preparative KR examples demonstrated the applicability of this method in the preparation of some of enantiomerically pure 2,2,2-trifluoro-1-aryl ethanol or 2,2,2-trifluoro-1-aryl-ethyl iso-butyrate.

Reduction of 2,2,2-trifluoro-1-arylethanones with alkyl phosphines

In the presence of alkyl phosphines, reduction of 2,2,2-trifluoro-1-arylethanones proceeded smoothly to give the corresponding reduction products in moderate to high yields at room temperature. The possible mechanism was discussed on the basis of deuteriu

Sodium trifluoroacetate: An efficient precursor for the trifluoromethylation of aldehydes

In a convenient and efficient procedure, the nucleophilic trifluoromethylation of aldehydes with sodium trifluoroacetate was achieved, using copper(I) halides as the catalyst.