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Organocatalytic Strategy for Hydrophenolation of Gem-Difluoroalkenes.

ABSTRACT: Gem-difluoroalkenes are an easily accessed fluorinated functional group, and a useful intermediate for elaborating into more complex fluorinated compounds. Currently, most functionalization reactions of gem-difluoroalkenes, with or without a transition metal-based catalyst system, involve the addition or removal of a fluorine atom to generate trifluorinated or monofluorinated products, respectively. In contrast, we present a complementary "fluorine-retentive" reaction that exploits an organocatalytic strategy to add phenols across gem-difluoroalkenes to deliver ?,?-difluorophenethyl arylethers. The products are produced in good to moderate yields and selectivities, thus providing a range of compounds that are underrepresented in the synthetic and medicinal chemistry literature.

SUBMITTER: Orsi DL

PROVIDER: S-EPMC7043310 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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Organocatalytic Strategy for Hydrophenolation of Gem-Difluoroalkenes.

Orsi Douglas L DL Yadav M Ramu MR Altman Ryan A RA

Tetrahedron 20190409 32

Gem-difluoroalkenes are an easily accessed fluorinated functional group, and a useful intermediate for elaborating into more complex fluorinated compounds. Currently, most functionalization reactions of gem-difluoroalkenes, with or without a transition metal-based catalyst system, involve the addition or removal of a fluorine atom to generate trifluorinated or monofluorinated products, respectively. In contrast, we present a complementary "fluorine-retentive" reaction that exploits ...[more]

PMID: 32103843

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