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Utilising Sodium-Mediated Ferration for Regioselective Functionalisation of Fluoroarenes via C-H and C-F Bond Activations
Authors:
Eva
Hevia
(University of Strathclyde)
,
Lewis C. H.
Maddock
(lewis.maddock@strath.ac.uk)
,
Tracy
Nixon
(University of Strathclyde)
,
Alan R.
Kennedy
(University of Strathclyde)
,
Michael R.
Probert
(Newcastle University)
,
William
Clegg
(Newcastle University)
Co-authored by industrial partner:
No
Type:
Journal Paper
Journal:
Angewandte Chemie International Edition
, VOL 57
, PAGES 187-191
State:
Published (Approved)
Published:
October 2017
Diamond Proposal Number(s):
11145
Abstract: 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.
Journal Keywords: metallation; mixed-metal chemistry; C-F bond activation; cascade processes; ferrates
Subject Areas:
Chemistry
Instruments:
I19-Small Molecule Single Crystal Diffraction