AgF-mediated fluorinative cross-coupling of two olefins: facile access to α-CF3 alkenes and β-CF3 ketones.
A AgF-mediated fluorination with a concomitant cross-coupling between a gem-difluoroolefin and a non-fluorinated olefin is reported. This highly efficient method provides facile access to both α-CF3 alkenes and β-CF3 ketones, which otherwise remain challenging to be directly prepared. The application of this method is further demonstrated by the synthesis of bioactive isoxazoline derivatives. This approach represents a conceptually novel route to trifluoromethylated compounds that combines the in situ generation of the CF3 moiety and a C-H functionalization in a single reaction system.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai, 200032 (China).
Bing
B
Gao
Yanchuan
Y
Zhao
Jinbo
J
Hu
D000475:Alkenes / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D018030:Silver Compounds / Q000737:chemistry*
D000475:Alkenes; D007659:Ketones; D018030:Silver Compounds; C105022:silver fluoride; D005459:Fluorides
alkenes; fluorination; fluorine; ketones; silver