Palladium-Catalyzed Cascade Reaction of Indoles with α,α-Difluoro-β,γ-Unsaturated Ketones: One-Step Access to 2-Fluorocarbazoles
Abstract
A practical synthesis of pharmacologically and materially relevant fluorinated carbazoles is highly desirable yet remains challenging. Herein, we report an efficient route to 2-fluorocarbazoles via a Pd(0)/Cu(I)-cocatalyzed tandem reaction between readily available α,α-difluoro-β,γ-unsaturated ketones and indoles. This protocol involves sequential Pd(0)-catalyzed defluorination and indole addition, followed by Cu(I)-promoted benzannulation. A variety of 2-fluorocarbazoles were obtained in good to excellent yields, and the synthetic utility was demonstrated by a gram-scale reaction. This method provides a practical and modular route to this valuable class of fluorinated heterocycles.
Fields of Study & Subjects
Fluorine in Organic Chemistry
Catalytic C–H Functionalization Methods
Synthesis and Characterization of Pyrroles
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 10
- Pages
- 3124–3129
- Publication date
- 2 March 2026
- Language
- EN