1005385-35-2

Upstream product

• 431-46-9 2,2,2-trifluoro-1-methoxy-ethanol 
• 94-09-7 p-aminoethylbenzoate 

Downstream Products

• 1005385-37-4 ethyl 4-[(2,2,2-trifluoroethyl)amino]benzoate 
• 1448324-00-2 (S)-ethyl 4-((2,2,2-trifluoro-1-(m-tolyl)ethyl)amino)benzoate 
• 1448323-92-9 (S)-ethyl 4-((2,2,2-trifluoro-1-phenylethyl)amino)benzoate 

Relevant academic research and scientific papers

Palladium(II)-catalyzed enantioselective synthesis of α- (trifluoromethyl)arylmethylamines

Trifluoromethylacetaldimines, generated in situ from the corresponding N,O-acetals, undergo 1,2-addition of arylboroxines under palladium(II) catalysis to generate a variety of α-(trifluoromethyl)arylmethylamines with good to high enantioselectivity (up to 97% ee). The pyridine-oxazolidine (PyOX) class of ligands was found to be particularly suitable for this transformation, which proceeds without exclusion of ambient air and moisture.

Trifluoroacetaldehyde: A useful industrial bulk material for the synthesis of trifluoromethylated amino compounds

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.