119561-19-2

Upstream product

• 434-45-7 2,2,2-Trifluoroacetophenone 
• 52826-45-6 (benzylimino)triphenylphosphorane 
• 100-46-9 benzylamine 

Downstream Products

• 13652-09-0 (RS)-1-phenyl-2,2,2-trifluoroethylamine hydrochloride 
• 1453102-07-2 C₁₅H₁₄F₃N 
• 1589570-35-3 (S)-N-(2,2,2-trifluoro-1-phenylethyl)acetamide 
• 22038-85-3 (R)-(-)-2,2,2-Trifluoro-1-phenylethylamine 
• 1035954-38-1 benzyl-[2,2,2-trifluoro-1-phenylethyl]amine 
• 1098215-29-2 N₁,N₂-dibenzyl-3,3,3-trifluoro-2-phenyl-N₂-(trifluoroacetyl)alaninamide 
• 1098215-44-1 ethyl N-benzyl-3,3,3-trifluoro-2-phenyl-N-(trifluoroacetyl)alanylglycinate 
• 51586-24-4 1-amino-2,2,2-trifluoro-1-phenylethane 
• 119561-20-5 N-benzylidene(1-phenyl-2,2,2-trifluoroethyl)amine 

Relevant academic research and scientific papers

Solid fly-ash:h2so4 catalyzed microwave assisted solvent-free condensation:synthesis of some trifluoromethyl-imines

Good yield of trifluoromethyl-imines have been synthesized by Fly-ash:H2SO4 catalyzed condensation of anilines and phenyl trifluoromethyl ketone in microwave irradiation under solvent free conditions.

Stereoselective metal-free catalytic synthesis of chiral trifluoromethyl aryl and alkyl amines

The enantioselective organocatalytic reduction of trifluoromethyl aryl and alkyl ketoimines afforded the corresponding fluorinated amines with high chemical and stereochemical efficiency. The Lewis base catalyzed reaction with trichlorosilane led to chiral products with a trifluoromethyl group directly linked to the newly generated stereocenter typically in >90% yield and up to 98% e.e.

Chemoenzymatic dynamic kinetic resolution of α-trifluoromethylated amines: Influence of substitutions on the reversed stereoselectivity

Enzymatic resolution of α-trifluoromethylated amines via kinetic resolution (KR), dynamic kinetic resolution (DKR) employing CALB-Pd/Al 2O3, and a one-pot sequential process of KR/DKR/KR was investigated comparatively for the first time. Although CALB-catalyzed KR of α-trifluoromethylated amines with substituents of methyl (1a), isopropyl (1c), phenyl (1d) and benzyl group (1e) can provide good stereoselectivity factors E from 31 to >200 respectively, DKR and sequential process of KR/DKR/KR possess better practical application potential because of the higher conversion (62%-84%) and the similar enantiomeric excesses (90%-99%). The enantiopreference and inversion for the α-trifluoromethylated amines displayed by CALB were observed and explained by docking modes. Namely, for 1,1,1-trifluoro-2-propylamine (1a), the product amide with R-configuration was obtained, and the enantiopreference was converted to S for the amines (1b-1e) with substituents larger than methyl group. The catalysts recycle, and scale-up experiments were demonstrated successfully. All these results indicated the high efficiency and green feature of this enzymatic process, and its application significance.

Expedient trimethylaluminium-promoted one-pot synthesis of functional heteroaromatic and carbocyclic trifluoroethylamines

The synthesis of trifluoroethylamines as amide bond mimics is an interesting topic in current research. They are well known tools in pharmaceutical and agrochemical industry. Other methods described in literature are often restricted to few substrates. We herein report a new synthetic approach towards this class of substances. First, the trimethylaluminium- promoted generation of a trifluoromethyl-ketimine from the corresponding trifluoromethyl ketone and an aniline derivative was investigated. Next, the ketimine was converted into the trifluoroethylamines in a one-pot reaction by simple addition of borane-methyl sulfide complex.

Diastereoselective alkylation of glycinates by assistance of intramolecular potassium-fluorine interactions

A study was conducted to demonstrate diatereoselective alkylation of glycinates by assistance of intermolecular potassium-fluorine interactions. Preparation of the starting materials for the investigations was carried out from the readily available fluorinated acetophenones. The investigations focused on finding appropriate alkylation conditions after their transformation to the corresponding enolates. The representative starting material was subjected to a solution of a base in THF at -78°C to generate the enolate. The model electrophile, BnBr was introduced in the investigations after stirring for 0.5 hours at the same temperature.

The Ugi reaction with CF3-carbonyl compounds: effective synthesis of α-trifluoromethyl amino acid derivatives

The Ugi reaction with CF3-carbonyl compounds is described in detail. The method is efficient for the multicomponent preparation of α-trifluoromethyl (Tfm) amino acids, α-Tfm containing dipeptides, and iminodicarboxylic acids. In addition, the first protected CF3-opine derivative was prepared. The scope, limitations, and stereochemistry of the approach are discussed.

Biomimetic reductive amination of fluoro aldehydes and ketones via [1,3]-proton shift reaction. Scope and limitations

A systematic study of azomethine-azomethine isomerizations of the N-benzylimines 2, derived from fluorinated aldehydes or ketones and benzylamine, has been made. The results reveal that, in sharp contrast to hydrocarbon analogs, fluorinated imines of 2 in triethylamine solution undergo isomerizations to give the corresponding N-benzylidene derivatives 5 (for 5/2 K > 32) in good isolated yields. The rates of the isomerizations depend on the starting imine structures and increase in the following order: aryl perfluoroalkyl ketimine 2m, per(poly)fluoroalkyl aldimine 2a,d-g, perfluoroaryl aldimine 2h, alkyl perfluoroalkyl ketimine 2i,j. The presence of chlorine or bromine atoms in the α-position to the C=N double bond of the starting imine favors a dehydrohalogenation reaction, giving rise to unsaturated products 6-9. The azomethine-azomethine isomerization was studied and proven to proceed essentially (>98%) intramolecularly with isotope exchange experiments. High chemical yields, the simplicity of the experimental procedure, and the low cost of all reagents employed make this biomimetic transamination of fluorocarbonyl compounds a practical method for preparing fluorine-containing amines of biological interest.

A practical route to fluoroalkyl- and fluoroarylamines by base-catalyzed [1,3]-proton shift reaction

The base-catalyzed [1,3]-proton shift reaction is shown to be an efficient general approach to fluoroalkyl and fluoroaryl amines starting from appropriate carbonyl compounds and benzylamine.

AZOMETHINE-AZOMETHINE ISOMERIZATION IN THE SERIES OF FLUORINE-CONTAINING N-BENZYLIMINES

The reaction of N-benzyltriphenylphosphine imide with fluorine-containing carbonyl compounds leads to the corresponding N-benzylimines.The latter readily isomerize under the influence of bases to N-benzylidene derivatives.