Reactivity of Aryl Trifluoromethyl Ketimines toward Organometallic Nucleophiles under Protic and Aprotic Conditions

The reactivity of aryl trifluoromethyl ketimines toward organometallic reagents was investigated and found that the reactivity of phenyl trifluoromethyl ketimine toward ^<i>n</i>BuLi is significantly higher than that of phenylglyoxylate imines under both on-water and conventional conditions. A variety of organolithium reagents underwent smooth 1,2-addition to aryl trifluoromethyl ketimines in THF at -78-0 °C, whereas Grignard reagents exhibited limited reactivity. These findings provide valuable insights for the development of efficient synthetic routes to trifluoromethylated amines, which are important motifs in medicinal chemistry.