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- Title
Utilising Sodium-Mediated Ferration for Regioselective Functionalisation of Fluoroarenes via C−H and C−F Bond Activations.
- Authors
Maddock, Lewis C. H.; Nixon, Tracy; Kennedy, Alan R.; Probert, Michael R.; Clegg, William; Hevia, Eva
- Abstract
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 80 °C switches on a remarkable cascade process inducing the collective twofold C−H/threefold C−F bond activations, where each C−H bond is transformed to a C−Fe bond whereas each C−F bond is transformed into a C−N bond.
- Subjects
SODIUM compounds; FERRITES synthesis; CARBON-hydrogen bonds; AROMATIC fluorine compounds; REGIOSELECTIVITY (Chemistry); INTERMEDIATES (Chemistry)
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 1, p193
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201709750