Related Experiment Video
Updated: Aug 21, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Transition Metal-Free Direct Trifluoromethylation of 2,3-Dihydropyridin-4(1H)-ones at Room Temperature
Yi-Yun Yu1, Adwait R Ranade2, Gunda I Georg1,2
1Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, United States.
Abstract:
A transition metal free, regioselective C5 trifluoromethylation of 2,3-dihydropyridine-4(1H)-ones (cyclic enaminones) with trimethyl(trifluoromethyl)silane (TMSCF3) was developed that proceeds under mild conditions at room temperature. This direct transformation was successful with both electron-rich and electron-deficient cyclic enaminones. This method bypasses substrate prefunctionalization and transition metal catalysis, and allows the convenient and direct access to a variety of medicinally important 3-trifluoromethylpiperidine derivatives. This chemistry also represents a rare example of a direct trifluoromethylation of an internal olefinic C-H bond. A radical mechanism is proposed for this reaction.
More Related Videos
07:14Experimental Approaches for the Synthesis of Low-Valent Metal-Organic Frameworks from Multitopic Phosphine Linkers
Published on: May 12, 2023
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Preparation and Reactions of Sulfides
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview