Morpholine-mediated defluorinative cycloaddition of gem-difluoroalkenes and organic azides

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 containing a morpholine adduct of gem-difluoroalkenes prior to triazolization reaction via two plausible pathways. Attractive elements include regioselective and straightforward direct synthesis of fully substituted 1,2,3-triazoles, which are difficult to access, from readily available starting materials.