Organocatalytic strategy for hydrophenolation of gem-difluoroalkenes

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 (beta,beta-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. (C) 2019 Elsevier Ltd. All rights reserved.