Organocatalytic strategy for hydrophenolation of gem-difluoroalkenes |
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Authors: | Douglas L Orsi M Ramu Yadav Ryan A Altman |
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Institution: | The University of Kansas, Department of Medicinal Chemistry, Lawrence, KS, 66045, USA |
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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 β,β-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. |
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Keywords: | Corresponding author Difluoroalkene Hydrophenolation Organocatalysis Base catalysis Fluorination |
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