A quantitative empirical directing group scale for selectivity in iridium-catalysed hydrogen isotope exchange reactions

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Timofeeva, Daria S. and Lindsay, David M. and Kerr, William J. and Nelson, David J. (2020) A quantitative empirical directing group scale for selectivity in iridium-catalysed hydrogen isotope exchange reactions. Catalysis Science and Technology, 10 (21). pp. 7249-7255. ISSN 2044-4753 (https://doi.org/10.1039/D0CY01597K)

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Abstract

A palette of commonly used directing groups, including various pharmaceutically relevant nitrogen-containing heterocycles, are quantitatively ranked based on the results of intermolecular hydrogen isotope exchange competition reactions using two iridium complexes: [Ir(COD)(IMes)(PPh3)][BArF24] and [IrCl(COD)(IMes)]. The directing group power scales that have been constructed from these data reveal a wide range of reactivity covering four orders of magnitude. Intramolecular competition experiments have demonstrated that the obtained reactivity scale provides accurate predictions of regioselectivity within molecules with multiple competing directing groups. This work contributes to our understanding and control of regioselectivity in metal-catalysed C-H activation reactions.

ORCID iDs

Timofeeva, Daria S., Lindsay, David M. ORCID logoORCID: https://orcid.org/0000-0003-4498-5094, Kerr, William J. ORCID logoORCID: https://orcid.org/0000-0002-1332-785X and Nelson, David J. ORCID logoORCID: https://orcid.org/0000-0002-9461-5182;
  • Item type:Article
    ID code:73843
    Dates:
    Date
    Event
    7 November 2020
    Published
    4 September 2020
    Published Online
    3 September 2020
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:15 Sep 2020 13:51
    Last modified:12 Dec 2024 10:21
    URI:https://strathprints.strath.ac.uk/id/eprint/73843
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