Friedel-Crafts Reaction of N-Alkyl Trifluoroacetaldehyde Imine: Facile Synthesis of 1-Aryl-2,2,2-trifluoroethylamines

Yuefa Gong; Katsuya Kato; Hiroshi Kimoto

doi:10.1055/s-2000-6681

Synlett 2000; 2000(7): 1058-1060
DOI: 10.1055/s-2000-6681

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Friedel-Crafts Reaction of N-Alkyl Trifluoroacetaldehyde Imine: Facile Synthesis of 1-Aryl-2,2,2-trifluoroethylamines

Yuefa Gong^* , Katsuya Kato, Hiroshi Kimoto

^*National Industrial Research Institute of Nagoya, Hirate-cho, Kita-ku, Nagoya 462-8510, Japan

Abstract

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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.

Friedel-Crafts reaction - trifluoroacetaldehyde imine - boron trifluoride - synthesis - 1-aryl-2,2,2-trifluoroethyl amine

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