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

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Brown, Jack A. and Cochrane, Alison R. and Irvine, Stephanie and Kerr, William J. and Mondal, Bhaskar and Parkinson, John A. and Paterson, Laura C. and Reid, Marc and Tuttle, Tell and Andersson, Shalini and Nilsson, Göran N. (2014) The synthesis of highly active iridium(I) complexes and their application in catalytic hydrogen isotope exchange. Advanced Synthesis and Catalysis, 356 (17). pp. 3551-3562. ISSN 1615-4150 (https://doi.org/10.1002/adsc.201400730)

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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.

ORCID iDs

Brown, Jack A., Cochrane, Alison R., Irvine, Stephanie, Kerr, William J. ORCID logoORCID: https://orcid.org/0000-0002-1332-785X, Mondal, Bhaskar, Parkinson, John A. ORCID logoORCID: https://orcid.org/0000-0003-4270-6135, Paterson, Laura C., Reid, Marc ORCID logoORCID: https://orcid.org/0000-0003-4394-3132, Tuttle, Tell, Andersson, Shalini and Nilsson, Göran N.;
  • Item type:Article
    ID code:49161
    Dates:
    Date
    Event
    24 November 2014
    Published
    2 October 2014
    Published Online
    4 September 2014
    Accepted
    Notes:This is the accepted version of the following article: The synthesis of highly active iridium(I) complexes and their application in catalytic hydrogen isotope exchange, Brown, J. A., Cochrane, A. R., Irvine, S., Kerr, W., Mondal, B., Parkinson, J. A., Paterson, L., Reid, M., Tuttle, T., Andersson, S. & Nilsson, G. N. 2014 In : Advanced Synthesis and Catalysis., which has been published in final form at: http://onlinelibrary.wiley.com/doi/10.1002/adsc.201400730/
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Technology and Innovation Centre > Bionanotechnology
    Depositing user: Pure Administrator
    Date deposited:10 Sep 2014 11:15
    Last modified:02 Dec 2024 01:15
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/49161
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