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

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Abstract

A pallette 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 constructred 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.
Original languageEnglish
Number of pages7
JournalCatalysis Science and Technology
Early online date4 Sep 2020
DOIs
Publication statusE-pub ahead of print - 4 Sep 2020

Keywords

  • heterocycles
  • hydrogen isotope exchange
  • iridium complexes

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    Insights into mechanism and selectivity in ruthenium(II)-catalysed ortho-arylation reactions directed by Lewis basic groups

    McIntyre, J., Mayoral-Soler, I., Salvador Sedano, P., Poater, A. & Nelson, D. J., 1 Jun 2018, In : Catalysis Science and Technology.

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