C–H activation and hydrogen isotope exchange of aryl carbamates using iridium(I) complexes bearing chelating NHC-phosphine ligands

Renan Zorzatto, Paul T. Mulrainey, Marc Reid, Tell Tuttle, David M. Lindsay, William J. Kerr*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

Hydrogen isotope exchange (HIE) via C−H activation constitutes an efficient method for the synthesis of isotopically‐enriched compounds, which are crucial components of the drug discovery process and are extensively employed in mechanistic studies. A series of iridium(I) complexes, bearing a chelating phosphine‐N‐heterocyclic carbene ligand, was designed and synthesized for application in the catalytic HIE of challenging N‐ and O‐aryl carbamates. A broad range of substrates were labeled efficiently, and applicability to biologically‐relevant systems was demonstrated by labeling an ʟ‐tyrosine‐derived carbamate with excellent levels of deuterium incorporation. Combined theoretical and experimental studies unveiled intriguing mechanistic features within this process, in comparison to C−H activation and hydrogen isotope exchange catalyzed by monodentate Ir(I) NHC/phosphine complexes.
Original languageEnglish
Article numbere202403090
Number of pages8
JournalChemistry - A European Journal
Volume30
Issue number69
Early online date17 Sept 2024
DOIs
Publication statusPublished - 10 Dec 2024

Keywords

  • C-H functionalization
  • hydrogen isotope exchange
  • iridium
  • N-Heterocyclic carbene

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