Modular Defluorinative Annulation Enabled by a Dearomative Rearrangement: Diversified Synthesis of Azaheterocycles
Abstract
The development of efficient and rapid construction of diverse N-heterocyclic scaffolds from simple starting materials has stimulated sustained enthusiasm from the chemical community. Herein we report a diversity-oriented defluorinative annulation triggered by Lewis base-promoted hydroalkoxylation/[3, 3]-sigmatropic rearrangement of fluorinated O -alkenyl- N -arylhydroxylamines and activated alkynes with or without amine. This protocol provides an efficient platform to prepare a diverse range of unusual three-dimensional functionalized oxa-aza[4.3.3]propellane- and indoline-related scaffolds in a modular pattern, which can greatly expend the chemical space of [3,3]-sigmatropic rearrangements.
Fields of Study & Subjects
Fluorine in Organic Chemistry
Catalytic C–H Functionalization Methods
Synthesis of heterocyclic compounds
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 15
- Pages
- 4998–5003
- Publication date
- 6 April 2026
- Language
- EN