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Incorporation of the pentafluorosulfanyl group through common synthetic transformations

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Abstract

The incorporation of –SF5 group onto model amino acids has been achieved using commercially available synthons substituted with this group. This work investigates the influence of the –SF5 group on a variety of common synthetic transformations utilized in fields of bioconjugation and drug development, namely, amide coupling, reductive amination, diazo-coupling, and CuAAC “click” reactions. The influence of the novel substituent on the success of these common transformations is presented, and alternative approaches for those which proved unsatisfactory are proposed herein.

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Acknowledgements

We would like to thank the University of Technology of Sydney for supporting this study. HH gratefully acknowledges the Australian Government and the University of Technology Sydney for providing the Research Training Program Stipend. HH gratefully acknowledges the Australian Institute of Nuclear Science and Engineering for providing the Residential Student Scholarship. GP acknowledges the Australian National Imaging Facility. The authors also acknowledge Glen Surjadinata and Luke Hunter for useful discussion and assistance with MS data.

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Authors and Affiliations

  1. School of Mathematical and Physical Sciences, Faculty of Science, University of Technology Sydney, Broadway, NSW, 2007, Australia

    Hugh G. Hiscocks, Dylan Lee Yit & Alison T. Ung

  2. Australian Nuclear Science and Technology Organisation, Locked Bag 2001, Kirrawee DC, NSW, 2232, Australia

    Giancarlo Pascali

  3. School of Chemistry, University of New South Wales, Kensington, NSW, 2052, Australia

    Giancarlo Pascali

  4. Prince of Wales Hospital, Nuclear Medicine and PET, Randwick, NSW, 2031, Australia

    Giancarlo Pascali

Authors
  1. Hugh G. Hiscocks
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  2. Dylan Lee Yit
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  3. Giancarlo Pascali
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  4. Alison T. Ung
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Correspondence to Alison T. Ung.

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Hiscocks, H.G., Yit, D.L., Pascali, G. et al. Incorporation of the pentafluorosulfanyl group through common synthetic transformations. Monatsh Chem 152, 449–459 (2021). https://doi.org/10.1007/s00706-021-02760-4

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  • DOI: https://doi.org/10.1007/s00706-021-02760-4

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