Related Experiment Video
Updated: Aug 6, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Catalytic Decarboxylative Carboamination of 2-(Trifluoromethyl)acrylic Acid Using Oxime Esters via Photo/Thermal
Shu-Jie Chen1, You-Hong Li1, Zhi-Qing He1
1School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou510006, China.
Abstract:
α-Trifluoromethylamines are prevalent in medicinal chemistry, yet synthetic approaches from readily available feedstocks remain limited. Herein, we report a visible-light-induced decarboxylative carboamination of commercially available 2-(trifluoromethyl)acrylic acid with oxime esters, enabling access to α-trifluoromethylimines that can be readily diversified into various α-trifluoromethylamine derivatives. The reaction proceeds under mild conditions and tolerates alkyl-, aryl-, and alkenyl-substituted carboxylic acid oxime esters. Furthermore, mechanistic studies provide detailed insights into the underlying reaction pathway.
Related Concept Videos
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...

