110972-15-1Relevant articles and documents
Trifluoroacetaldehyde: A useful industrial bulk material for the synthesis of trifluoromethylated amino compounds
Mimura, Hideyuki,Kawada, Kosuke,Yamashita, Tetsuya,Sakamoto, Takeshi,Kikugawa, Yasuo
experimental part, p. 477 - 486 (2010/05/02)
The synthesis of various trifluoromethylated amino compounds was studied using trifluoroacetaldehyde, an industrial bulk material, as a starting compound. One general application of trifluoroacetaldehyde is the preparation of trifluoroethylamino derivatives via reductive amination reaction. This synthesis includes the formation of the corresponding N,O-acetal intermediates followed by their reduction using NaBH4 or 2-picoline borane complex, affording the target trifluoroethylamino compounds in moderate to good yields (47-87%). Another general application of trifluoroacetaldehyde is the synthesis of chiral α-substituted trifluoroethylamino compounds. In this synthesis, trifluoroacetaldehyde was first converted into the chiral trifluoromethyl tert-butyl sulfinimine, which was subjected to 1,2-nucleophilic addition reactions across its C{double bond, long}N double bond. The addition of phenyllithium afforded α-(phenyl)trifluoroethylamino derivative in 83% yield and with 96% de. Allylation and Reformatsky reactions produced the corresponding α-substituted trifluoroethylamino derivatives in 82 and 58% yields and with 90 and 91% de, respectively.
Electrolytic Transformation of Fluoroorganic Compounds. 3. Highly Regioselective Anodic Methoxylation of N-(2,2,2-trifluoroethyl)amines
Fuchigami, Toshio,Nakagawa, Yuuki,Nonaka, Tsutomu
, p. 5489 - 5491 (2007/10/02)
Anodic methoxylation of N-alkyl-N-(2,2,2-trifluoroethyl)anilines and N-(2,2,2-trifluoroethyl)diphenylamine places the methoxy group in the α-position (toward the trifluoromethyl group); these products are useful building blocks for the construction of a c