The synthesis of highly active iridium(I) complexes and their application in catalytic hydrogen isotope exchange

Jack A. Brown, Alison Ruth Cochrane, Stephanie Irvine, William J. Kerr, Bhaskar Mondal, John A. Parkinson, Laura Paterson, Marc Reid, Tell Tuttle, Shalini Andersson, Göran N. Nilsson

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Abstract

A series of robust iridium(I) complexes bearing a sterically encumbered N-heterocyclic carbene ligand, alongside a phosphine ligand, has been synthesised and investigated in hydrogen isotope exchange processes. These complexes have allowed isotope incorporation over a range of substrates with the use of practically convenient deuterium and tritium gas. Moreover, these active catalysts are capable of isotope incorporation to particularly high levels, whilst employing low catalyst loadings and in short reaction times. In addition to this, these new catalyst species have shown flexible levels of chemoselectivity, which can be altered by simple manipulation of preparative approaches. Furthermore, a number of industrially-relevant drug molecules have also been labelled, including the sulfonamide containing drug, Celecoxib. Alongside detailed NMR experiments, initial mechanistic investigations have also been performed, providing insight into both substrate binding energies, and, more importantly, relative energies of key steps in the mechanistic cycle as part of the overall exchange process.
Original languageEnglish
Pages (from-to)3551-3562
Number of pages12
JournalAdvanced Synthesis and Catalysis
Volume356
Issue number17
Early online date2 Oct 2014
DOIs
Publication statusPublished - 24 Nov 2014

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Keywords

  • hydrogen isotope exchange
  • iridium
  • catalysis
  • deuterium
  • tritium

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