Utilising sodium-mediated ferration for regioselective functionalisation of fluoroarenes via C-H and C-F bond activations

Lewis C. H. Maddock, Tracy Nixon, Alan R. Kennedy, Michael R. Probert, William Clegg, Eva Hevia

Research output: Contribution to journalArticle

8 Citations (Scopus)
12 Downloads (Pure)

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 80oC switches on a remarkable cascade process inducing the collective 2-fold C-H/3-fold 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.
Original languageEnglish
Pages (from-to)187-191
Number of pages5
JournalAngewandte Chemie International Edition
Volume57
Issue number1
Early online date25 Oct 2017
DOIs
Publication statusPublished - 27 Dec 2017

Keywords

  • metallation
  • mixed-metal chemistry
  • C-F bond activation
  • cascade processes
  • ferrates

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