3 years ago

Utilising Sodium-Mediated Ferration for Regioselective Functionalisation of Fluoroarenes via C-H and C-F Bond Activations

Alan R Kennedy, Michael R Probert, Lewis C. H. Maddock, Eva Hevia, Tracy Nixon, William Clegg
While Fe(II) complexes have shown little promise in deprotonative metallation chemistry, pairing iron bis(amide) Fe(HMDS)2 with Na(HMDS) to form new sodium ferrate base [(dioxane)0.5·NaFe(HMDS)3] (1) enables regioselective mono and di-ferration (via direct Fe-H exchange) of a wide range of fluoroaromatic substrates under mild reaction conditions. Trapping of several ferrated intermediates has provided key insight into how synchronised Na/Fe cooperation operates in these transformations. Furthermore using excess 1 at 80oC switches on a remarkable cascade process inducing the collective 2-fold C-H/3-fold C-F bond activation, where each C-H bond is transformed to C-Fe bonds whereas each C-F bond is transformed into a C-N bond.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201709750

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