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Quantitative Prediction of Selectivity in Iridium-Catalysed Hydrogen Isotope Exchange Reactions

preprint
submitted on 30.06.2020 and posted on 02.07.2020 by Daria Timofeeva, David Lindsay, William Kerr, David Nelson
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.

Funding

Leverhulme Trust RPG-2018-207

History

Email Address of Submitting Author

david.nelson@strath.ac.uk

Institution

University of Strathclyde

Country

Scotland

ORCID For Submitting Author

0000-0002-9461-5182

Declaration of Conflict of Interest

No conflict of interest

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