C–H activation and hydrogen isotope exchange of aryl carbamates using iridium(I) complexes bearing chelating NHC-phosphine ligands
Zorzatto, Renan and Mulrainey, Paul and Reid, Marc and Tuttle, Tell and Lindsay, David and Kerr, William J. (2024) C–H activation and hydrogen isotope exchange of aryl carbamates using iridium(I) complexes bearing chelating NHC-phosphine ligands. Chemistry - A European Journal. ISSN 1521-3765 (https://doi.org/10.1002/chem.202403090)
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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 catalysed by monodentate Ir(I) NHC/phosphine complexes.
ORCID iDs
Zorzatto, Renan ORCID: https://orcid.org/0000-0002-6923-7837, Mulrainey, Paul, Reid, Marc ORCID: https://orcid.org/0000-0003-4394-3132, Tuttle, Tell, Lindsay, David ORCID: https://orcid.org/0000-0003-4498-5094 and Kerr, William J. ORCID: https://orcid.org/0000-0002-1332-785X;-
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Item type: Article ID code: 90613 Dates: DateEvent17 September 2024Published17 September 2024Published Online17 September 2024AcceptedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry
Technology and Innovation Centre > BionanotechnologyDepositing user: Pure Administrator Date deposited: 20 Sep 2024 13:33 Last modified: 01 Oct 2024 07:05 URI: https://strathprints.strath.ac.uk/id/eprint/90613