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

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.

Beilstein J. Org. Chem. 2023, 19, 1545–1554. doi:10.3762/bjoc.19.111

Source: Beilstein Journal of Organic Chemistry - October 5, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: [3 2] cycloaddition defluorination fully decorated 1,2,3-triazoles gem-difluoroalkenes organic azides Letter Source Type: research