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Updated: Jul 13, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Morpholine-mediated defluorinative cycloaddition of gem-difluoroalkenes and organic azides
Tzu-Yu Huang1, Mario Djugovski1, Sweta Adhikari1
1Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, MS 38677, USA.
Abstract:
Here, we report the first transition-metal-free defluorinative cycloaddition of gem-difluoroalkenes with organic azides in morpholine as a solvent to construct fully decorated morpholine-substituted 1,2,3-triazoles. Mechanistic studies revealed the formation of an addition-elimination intermediate of morpholine and gem-difluoroalkenes prior to the triazolization reaction via two plausible pathways. Attractive elements include the regioselective and straightforward direct synthesis of fully substituted 1,2,3-triazoles, which are otherwise difficult to access, from readily available starting materials.
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