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Updated: Jan 10, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Bifunctional Aziridines from Photochemically Generated FSO2NH2 for SuFEx Diversification of Alkenes
Avinash Choudhury1, Varun Prabhakar1, Zakary B Newman1
1Department of Chemistry, Texas A & M University, College Station, Texas, 77843, USA.
Researchers developed a new method to synthesize sulfamoyl fluorides using fluorosulfonyl aziridines. This breakthrough enables versatile alkene diversification and creates novel S(VI)-containing linkages for pharmaceutical applications.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Materials Science
Background:
- Sulfonyl fluorides are key reactive groups in chemistry.
- Sulfur(VI) Fluoride Exchange (SuFEx) click chemistry offers modularity.
- Methods for incorporating sulfamoyl fluorides into complex molecules are limited.
Purpose of the Study:
- To develop a versatile platform for synthesizing sulfamoyl fluorides.
- To enable alkene diversification using a novel approach.
- To explore new S(VI)-containing linkages for pharmaceutical relevance.
Main Methods:
- Optimized a safe synthesis of fluorosulfonyl amine (FSO2NH2) via photodegradation of fluorosulfonyl azide.
- Developed a Rh-catalyzed aziridination reaction with broad alkene scope.
- Utilized the resulting fluorosulfonyl aziridines as bifunctional electrophiles.
Main Results:
- Successfully synthesized fluorosulfonyl aziridines from FSO2NH2.
- Demonstrated a modular platform for alkene diversification.
- Achieved selective reactions with various nucleophiles under mild conditions.
- Produced sulfamoyl fluorides, sulfamides, and sulfamate esters.
Conclusions:
- Fluorosulfonyl aziridines provide a versatile and modular approach to sulfamoyl fluoride synthesis.
- This method expands the utility of SuFEx chemistry.
- The developed reactions yield pharmaceutically relevant S(VI)-containing linkages.
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