PPh 3 -Catalyzed Remote Aminofluorination Reactions: Regioselective Access to γ- and ε-Fluoroamines Containing Oxindole
Abstract
Remote aminofluorinations as a powerful strategy to synthesize 1, n -fluoroamines ( n > 2) are of great significance and highly challenging. Herein, a remote 1,5-aminofluorination of spirovinylcyclopropyl oxindoles and N -fluorobenzenesulfonimide (NFSI) was achieved by using PPh 3 as a catalyst, affording ε-fluoroamines containing oxindole (up to 60% yield, all >20:1 E: Z ). As opposed to the traditional choice, TMSCN was used as an additive, which makes the reaction a dramatic shift to the 1,3-aminofluorination of spirovinylcyclopropyl oxindoles, and γ-fluoroamines containing oxindole were obtained with high diastereoselectivity and high yield (up to 99%). Based on experimental results and high-resolution mass spectrometry experiments, a plausible reaction mechanism is proposed.
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
- 11
- Pages
- 3659–3664
- Publication date
- 4 March 2026
- Language
- EN