Utilising Sodium‐Mediated Ferration for Regioselective Functionalisation of Fluoroarenes via C−H and C−F Bond Activations |
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| Authors: | Dr Lewis C H Maddock Dr Tracy Nixon Dr Alan R Kennedy Dr Michael R Probert Prof William Clegg Prof Eva Hevia |
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| Institution: | 1. WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, UK;2. Chemistry, School of Natural and Environmental Sciences, Newcastle University, Newcastle upon Tyne, UK |
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| 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. |
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| Keywords: | alkali metals C− F bond activation iron metalation mixed-metal chemistry |
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