期刊
TETRAHEDRON
卷 75, 期 32, 页码 4325-4336出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.04.016
关键词
Difluoroalkene; Hydrophenolation; Organocatalysis; Base catalysis; Fluorination
资金
- Herman Frasch Foundation for Chemical Research [701-HF12]
- National Institutes of Health [R35 GM124661]
- Madison and Lila Self Graduate Fellowship
- NIH [S10OD016360, S10RR024664]
- NSF Major Research Instrumentation Grants [9977422, 0320648]
- NIH Center Grant [P20GM103418]
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.
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