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.
Keywords: alkenes; fluorination; fluorine; ketones; silver.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.