1997-85-9

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 29, p. 2061, 1964 DOI: 10.1021/jo01030a536

InChI:InChI=1/C9H8F3N/c10-9(11,12)7-13-6-8-4-2-1-3-5-8/h1-5,7H,6H2

Upstream product

• 100-46-9 benzylamine 
• 433-27-2 ethyl trifluoroacetaldehyde hemiacetal 
• 431-46-9 2,2,2-trifluoro-1-methoxy-ethanol 
• 75-90-1 2,2,2-Trifluoroacetaldehyde 

Downstream Products

• 294174-92-8 benzyl[2,2,2-trifluoro-1-(1H-indol-3-yl)ethyl]amine 
• 294174-94-0 benzyl[2,2,2-trifluoro-1-(1H-pyrrol-2-yl)ethyl]amine 
• 511522-21-7 benzyl[2,2,2-trifluoro-1-(1-methyl-1H-pyrrol-3-yl)ethyl]amine 
• 511522-20-6 benzyl[2,2,2-trifluoro-1-(1-methyl-1H-pyrrol-2-yl)ethyl]amine 
• 592537-90-1 N-benzyl-1,1,1-trifluoro-4-methyl-4-penten-2-amine 
• 592538-19-7 N-benzyl-1,1,1-trifluoro-4-penten-2-amine 
• 592537-87-6 N-benzyl-1,1,1-trifluoro-3,3-dimethyl-4-penten-2-amine 
• 612548-92-2 N-allyl-N-benzyl[3-methyl-1-(trifluoromethyl)but-3-enyl]amine 
• 852945-12-1 N-benzyl-N-prop-2-ynyl[1-(trifluoromethyl)but-3-enyl]amine 
• 612548-93-3 N-allyl-N-benzyl[2,2-dimethyl-1-(trifluoromethyl)but-3-enyl]amine 
• 612548-88-6 benzyl[1-(trifluoromethyl)but-3-ynyl]amine 

Relevant academic research and scientific papers

Nucleophile-directed selective transformation of cis-1-tosyl-2- tosyloxymethyl-3-(trifluoromethyl)aziridine into aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines

A five-step procedure for the synthesis of cis-1-tosyl-2-tosyloxymethyl-3- (trifluoromethyl)aziridine was developed, starting from 1-ethoxy-2,2,2- trifluoroethanol, involving imination, aziridination, ester reduction, hydrogenation, and N-,O-ditosylation steps. Further synthetic elaborations revealed a remarkable difference in the reactivity of cis-1-tosyl-2- tosyloxymethyl-3-(trifluoromethyl)aziridine with respect to aromatic sulfur and oxygen nucleophiles, thus enabling the selective deployment of this versatile substrate as a building block for the synthesis of functionalized aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines. Copyright

N-Ammonium Ylide Mediators for Electrochemical C-H Oxidation

The site-specific oxidation of strong C(sp3)-H bonds is of uncontested utility in organic synthesis. From simplifying access to metabolites and late-stage diversification of lead compounds to truncating retrosynthetic plans, there is a growing need for new reagents and methods for achieving such a transformation in both academic and industrial circles. One main drawback of current chemical reagents is the lack of diversity with regard to structure and reactivity that prevents a combinatorial approach for rapid screening to be employed. In that regard, directed evolution still holds the greatest promise for achieving complex C-H oxidations in a variety of complex settings. Herein we present a rationally designed platform that provides a step toward this challenge using N-ammonium ylides as electrochemically driven oxidants for site-specific, chemoselective C(sp3)-H oxidation. By taking a first-principles approach guided by computation, these new mediators were identified and rapidly expanded into a library using ubiquitous building blocks and trivial synthesis techniques. The ylide-based approach to C-H oxidation exhibits tunable selectivity that is often exclusive to this class of oxidants and can be applied to real-world problems in the agricultural and pharmaceutical sectors.

Formylation of fluoroalkyl imines through visible-light-enabled H-atom transfer catalysis: Access to fluorinated α-amino aldehydes

A visible-light-enabled catalytic formylation of fluoroalkyl imines is developed. With readily accessible starting materials and organocatalysts, this method provides a general approach to masked fluoroalkyl amino aldehydes. A synergistic catalytic effect

Trifluoromethyl syn- or anti-γ-amino alcohols by one-pot solvent-free Mannich-type reactions under temperature control

Starting from trifluoroacetaldehyde ethyl hemiacetal, chiral amines and suitable aldehydes, diastereomerically pure fluorinated syn- or anti-γ-amino alcohols can be obtained by a friendly one-pot solvent-free l-proline catalysed Mannich-type reaction only

Highly diastereo- and enantioselective vinylogous Mannich reactions of fluorinated aldimines with siloxyfurans

A highly regio- and enantioselective asymmetric vinylogous Mannich reaction of readily available fluorinated aldimines bearing a chiral auxiliary [(S)-1-phenylethyl group] with siloxyfurans to afford chiral fluorine-containing γ-butenolide or γ-lactone derivatives has been developed in the presence of silver acetate (10 mol%) and axially chiral phosphine-oxazoline ligand L1 (11 mol%). In most cases, the corresponding fluorinated adducts were obtained in high yields, good to excellent enantiomeric excesses and up to > 20:1 dr.

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.

BF3-promoted aromatic substitution of N-alkyl α-trifluoromethylated imine: Facile synthesis of 1-aryl-2,2,2-trifluoroethylamines

The aromatic substitution of three representative N-alkyl trifluoromethyl imines 1a-c (R: a, benzyl; b, benzhydryl; c, methyl), obtained from primary alkyl amines and trifluoroacetaldehyde ethyl hemiacetal, was used to investigate the preparation of 1-aryl-2,2,2-trifluoroethylamines. In the presence of BF3·OEt2, the reaction of imine 1 with various aromatic compounds proceeded smoothly at room temperature, giving N-alkyl-1-aryl-2,2,2-trifluoroethylamines in moderate-to-high yields. Moreover, successful regioselective removal of N-benzyl and N-benzhydryl groups was achieved by hydrolysis in hydrochloric acid or by palladium-catalyzed hydrogenolysis.

Friedel-Crafts reaction of N-alkyl trifluoroacetaldehyde imine: Facile synthesis of 1-aryl-2,2,2-trifluoroethylamines

N-Alkyl trifluoroacetaldehyde imines 1a,b (R: a, benzyl; b, diphenylmethyl), prepared from trifluoroacetaldehyde ethyl hemiacetal (TFAE) and primaryl amines, readily reacted with electron-rich heteroarenes, N,N- dimethylaniline and phenols in the presence of BF3. Product analysis showed moderate to high yields of N-alkyl-1-aryl-2,2,2-trifluoroethylamines 2-7. Hydrolysis of representative N-diphenylmethyl amines 5b and 7b, respectively yielded the 1-aryl-2,2,2-trifluoroethylamines 10 and 11.

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.