American Chemical Society
ol401558z_si_001.pdf (3.66 MB)

Silver-Mediated Methoxycarbonyltetrafluoroethylation of Arenes

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journal contribution
posted on 2013-07-05, 00:00 authored by Andreas Hafner, Thomas J. Feuerstein, Stefan Bräse
In the presence of silver(I) fluoride, highly fluorinated olefins react readily under solvent-free conditions with arenes via CH-substitution. This transformation could be used to synthesize various methoxycarbonyltetrafluoroethylated aromatic triazenes and anisoles under high functional group tolerance. The method could be applied to the synthesis of a formal fluorinated bioisostere of the NSAID flurbiprofen. To the best of our knowledge, this is the first example which uses highly fluorinated olefins for the perfluoroalkylation of aromatic substrates.