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

Research output: Contribution to journalArticlepeer-review

2 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)7249-7255
Number of pages7
JournalCatalysis Science and Technology
Volume10
Issue number21
Early online date4 Sep 2020
DOIs
Publication statusPublished - 7 Nov 2020

Keywords

  • heterocycles
  • hydrogen isotope exchange
  • iridium complexes

Fingerprint Dive into the research topics of 'A quantitative empirical directing group scale for selectivity in iridium-catalysed hydrogen isotope exchange reactions'. Together they form a unique fingerprint.

Cite this