Triplet Energy Transfer-Mediated Intermolecular Paternò–Büchi Reaction for the Synthesis of Trifluoromethylated Oxetanes
Abstract
High Resolution Image Download MS PowerPoint Slide Oxetanes are increasingly used as compact, polar carbonyl (bio)isosteres in drug discovery, and the combination with a trifluoromethyl group enables fine-tuning of molecular properties. Here, we report a visible-light-mediated Paternò–Büchi strategy that accesses CF 3 -containing oxetanes via triplet-energy-transfer activation and delivers a broad range of CF 3 -containing oxetane products with excellent regio- and diastereoselectivity. Mechanistic studies indicate that although sensitization of both the alkene and carbonyl occurs in solution, the subsequent stepwise [2 + 2] cycloaddition proceeds preferentially from the triplet excited state of the CF 3 -substituted carbonyl partner.
Fields of Study & Subjects
Fluorine in Organic Chemistry
Radical Photochemical Reactions
Synthesis and Catalytic Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 11
- Pages
- 3388–3393
- Publication date
- 5 March 2026
- Language
- EN