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

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Maddock, Lewis C. H. and Nixon, Tracy and Kennedy, Alan R. and Probert, Michael R. and Clegg, William and Hevia, Eva (2017) Utilising sodium-mediated ferration for regioselective functionalisation of fluoroarenes via C-H and C-F bond activations. Angewandte Chemie International Edition, 57 (1). pp. 187-191. ISSN 1521-3773 (https://doi.org/10.1002/anie.201709750)

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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 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.

ORCID iDs

Maddock, Lewis C. H. ORCID logoORCID: https://orcid.org/0000-0001-7446-6565, Nixon, Tracy, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Probert, Michael R., Clegg, William and Hevia, Eva ORCID logoORCID: https://orcid.org/0000-0002-3998-7506;
  • Item type:Article
    ID code:62459
    Dates:
    Date
    Event
    27 December 2017
    Published
    25 October 2017
    Published Online
    25 October 2017
    Accepted
    Notes:This is the peer reviewed version of the following article: Maddock, LCH, Nixon, T, Kennedy, AR, Probert, MR, Clegg, W & Hevia, E 2017, 'Utilising sodium-mediated ferration for regioselective functionalisation of fluoroarenes via C-H and C-F bond activations' Angewandte Chemie International Edition, which has been published in final form at https://doi.org/10.1002/anie.201709750. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:28 Nov 2017 17:08
    Last modified:14 Dec 2024 03:24
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/62459
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