Trifluoroacetylation of Anilines with Ethyl Trifluoropyruvate Mediated by Copper(I) Chloride

Abstract

A novel copper(I)-mediated trifluoroacetylation of anilines with ethyl trifluoropyruvate as a trifluoroacetylating reagent has been developed. Although this protocol could provide good yields in most cases, the reaction exhibited the obvious electronic and steric effects of substituents. The trace amount of products was only obtained for the substrates with ortho-substituted or electron-deficient groups.

Copper-mediated three-component synthesis of 2-trifluoromethyl benzimidazoles

“…Furthermore, trifluoroacetylation of aniline 2a with 3a led to the formation of the trifluoroacetylated intermediate 2,2,2-trifluoro-N-phenylacetamide (7). 48 The subsequent reaction of 7 with 1a under standard conditions failed to initiate the reaction, clearly indicating that the reaction was not proceeding through the trifluoroacetylation of aniline (Scheme 4b). The trifluoroacetylation of o-iodoaniline 1a with 3a resulted in the formation of another trifluoroacetylated intermediate 2,2,2-trifluoro-N-(2-iodophenyl)acetamide (8) in only 6% yield.…”