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A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis.

ABSTRACT: The vicinal fluorofunctionalization of alkenes represents an expedient strategy for converting feedstock olefins into valuable fluorinated molecules and as such has garnered significant attention from the synthetic community; however, current methods remain limited in terms of scope and selectivity. Here we report the site-selective palladium-catalyzed three-component coupling of alkenylbenzaldehydes, arylboronic acids, and N-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate facilitated by a transient directing group. The synthetically enabling methodology constructs vicinal stereocenters with excellent regio-, diastereo-, and enantioselectivities, forging products that map onto bioactive compounds.

SUBMITTER: Liu Z

PROVIDER: S-EPMC8222155 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis.

Liu Zhonglin Z Oxtoby Lucas J LJ Liu Mingyu M Li Zi-Qi ZQ Tran Van T VT Gao Yang Y Engle Keary M KM

Journal of the American Chemical Society 20210602 24

The vicinal fluorofunctionalization of alkenes represents an expedient strategy for converting feedstock olefins into valuable fluorinated molecules and as such has garnered significant attention from the synthetic community; however, current methods remain limited in terms of scope and selectivity. Here we report the site-selective palladium-catalyzed three-component coupling of alkenylbenzaldehydes, arylboronic acids, and N-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate facilitate ...[more]

PMID: 34077182

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