TBADT-Photocatalyzed Trifluoromethylation of Phenylpropiolamides Using Langlois Reagent: Access to Oxindole Derivatives
Abstract
In this study, we report the radical-mediated trifluoromethylation of phenylpropiolamides using the Langlois reagent (CF 3 SO 2 Na) under ultraviolet light irradiation, with tetrabutylammonium decatungstate (TBADT) serving as an efficient inorganic photocatalyst. This method synthesizes a wide range of oxindoles by generating a CF 3 radical, which induces an intermolecular C–CF 3 bond (via a Michael addition on the propiolamide moiety), followed by an intramolecular C–C bond formation and reduction sequence. Thus, a broad range of trifluoromethyl-substituted oxindoles have been accomplished in high yields under mild conditions.
Fields of Study & Subjects
Fluorine in Organic Chemistry
Radical Photochemical Reactions
Advanced Synthetic Organic Chemistry
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 10
- Pages
- 3855–3870
- Publication date
- 3 March 2026
- Language
- EN