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A Base-Promoted Reductive Coupling Platform for the Divergent Defluorofunctionalization of Trifluoromethylarenes.

ABSTRACT: We report a trifluoromethylarene reductive coupling method that dramatically expands the scope of difluorobenzylic substructures accessible via C-F bond functionalization. Catalytic quantities of a Lewis base, combined with a disilane reagent in formamide solvent, promotes the replacement of a single trifluoromethyl fluorine atom with a silylated hemiaminal functional group. The reaction proceeds through a difluorobenzyl silane intermediate that can also be isolated. Together, these defluorinated products are shown to provide rapid access to over 20 unique difluoroalkylarene scaffolds.

SUBMITTER: Wright SE

PROVIDER: S-EPMC9817215 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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A Base-Promoted Reductive Coupling Platform for the Divergent Defluorofunctionalization of Trifluoromethylarenes.

Wright Shawn E SE Bandar Jeffrey S JS

Journal of the American Chemical Society 20220714 29

We report a trifluoromethylarene reductive coupling method that dramatically expands the scope of difluorobenzylic substructures accessible <i>via</i> C-F bond functionalization. Catalytic quantities of a Lewis base, combined with a disilane reagent in formamide solvent, promotes the replacement of a single trifluoromethyl fluorine atom with a silylated hemiaminal functional group. The reaction proceeds through a difluorobenzyl silane intermediate that can also be isolated. Together, these deflu ...[more]

PMID: 35833781

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