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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.

SUBMITTER: Huang TY

PROVIDER: S-EPMC10562644 | biostudies-literature | 2023

REPOSITORIES: biostudies-literature

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

Huang Tzu-Yu TY Djugovski Mario M Adhikari Sweta S Manning Destinee L DL Roy Sudeshna S

Beilstein journal of organic chemistry 20231005

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 ...[more]

PMID: 37822920

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