294174-93-9Relevant academic research and scientific papers
BF3-promoted aromatic substitution of N-alkyl α-trifluoromethylated imine: Facile synthesis of 1-aryl-2,2,2-trifluoroethylamines
Gong, Yuefa,Kato, Katsuya,Kimoto, Hiroshi
, p. 2637 - 2645 (2007/10/03)
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.
Convenient preparation of 1-(indol-3-yl)-2,2,2-trifluoroethylamines via Friedel-Crafts reaction of α-trifluoroacetaldehyde hemiaminal
Gong,Kato
, p. 83 - 86 (2007/10/03)
Electrophilic substitution of indole with trifluoroacetaldehyde hemiaminals 1a-f, prepared from primary amines and trifluoroacetaldehyde ethyl hemiacetal (TFAE), proceeds readily in the presence of Lewis acids. Formation of N-alkyl 1-(indol-3-yl)-2,2,2-trifluoroethylamines (2) is preferred in the presence of BF3, but yield of 2,2,2-trifluoroethyl alcohol (3) markedly increases when ZnI2 is used. A stereochemistry study clearly showed that ethylamines 2e and 2f are produced with high diastereoselective excess when the optically active hemiaminals 1e and 1f are used.
Friedel-Crafts reaction of N-alkyl trifluoroacetaldehyde imine: Facile synthesis of 1-aryl-2,2,2-trifluoroethylamines
Gong, Yuefa,Kato, Katsuya,Kimoto, Hiroshi
, p. 1058 - 1060 (2007/10/03)
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.
