[4 + 2] Annulation of CF 3 -π-Allyl–Pd Species with Isatic Acids for Direct Access to 3-Trifluoroethyl-4-carboxylate Quinolines
Abstract
Herein, we report a catalytic [4 + 2] annulation between trifluoromethyl allyl carbonates and isatic acids that provides direct access to 3-trifluoroethyl-4-carboxylate quinolines. The transformation proceeds smoothly under mild conditions and accommodates a broad range of electron-donating, electron-withdrawing, and sterically demanding substituents. In addition, a one-pot protocol enables efficient conversion of the annulation products into 3-trifluoroethyl-4-amido quinolines under the same reaction conditions. The synthetic versatility of this strategy is further demonstrated through the one-pot preparation of a trifluoroethyl analogue of brequinar, as well as the streamlined synthesis of trifluoroethylated analogues of bioactive scaffolds.
Fields of Study & Subjects
Fluorine in Organic Chemistry
Cyclopropane Reaction Mechanisms
Radical Photochemical Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 7
- Pages
- 2306–2311
- Publication date
- 9 February 2026
- Language
- EN