Related Experiment Video
Updated: Jan 11, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Reactivity of Aryl Trifluoromethyl Ketimines toward Organometallic Nucleophiles under Protic and Aprotic Conditions
Yoshihiko Yamamoto1, Hirotaka Uchida1, Ryu Tadano1
1Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
Abstract:
The reactivity of aryl trifluoromethyl ketimines toward organometallic reagents was investigated and found that the reactivity of phenyl trifluoromethyl ketimine toward nBuLi 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.
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Nitriles to Ketones: Grignard Reaction
The mechanism begins with a nucleophilic attack by the Grignard...
Nucleophilic Aromatic Substitution: Elimination–Addition
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
α-Alkylation of Ketones via Enolate Ions
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...

