Related Experiment Video
Updated: Apr 7, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Modular Defluorinative Annulation Enabled by a Dearomative Rearrangement: Diversified Synthesis of Azaheterocycles
Lei Yang1, Lei Huang1, Zhong-Lin Wei1
1Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. China.
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.
More Related Videos
Related Concept Videos
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

