Organocatalytic Strategy for Hydrophenolation of -Difluoroalkenes.

Tetrahedron

The University of Kansas, Department of Medicinal Chemistry, Lawrence, KS 66045.

Published: August 2019

-difluoroalkenes are an easily accessed fluorinated functional group, and a useful intermediate for elaborating into more complex fluorinated compounds. Currently, most functionalization reactions of -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 -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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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7043310PMC
http://dx.doi.org/10.1016/j.tet.2019.04.016DOI Listing

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