Utilising Sodium‐Mediated Ferration for Regioselective Functionalisation of Fluoroarenes via C−H and C−F Bond Activations. (30th November 2017)

• Record Type: Journal Article
• Authors: Maddock, Lewis C. H.; Nixon, Tracy; Kennedy, Alan R.; Probert, Michael R.; Clegg, William; Hevia, Eva
• Is Part Of: Angewandte Chemie. Volume 130:Number 1(2018)
• Page Start: 193
• Page End: 197
• Publication Date: 2017-11-30
• Subjects: Alkalimetalle -- C-F-Aktivierung -- Eisen -- Heterometallreagentien -- Metallierungen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201709750
• Languages: English
• ISSNs: 0044-8249

Abstract

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 excess1 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.