Skip to content

Research at St Andrews

Mild, aqueous α-arylation of ketones: towards new diversification tools for halogenated metabolites and drug molecules

Research output: Contribution to journalArticle

DOI

Author(s)

Enrico Marelli, Yohann Renault, Sunil V. Sharma, Steven P. Nolan, Rebecca J. M. Goss

School/Research organisations

Abstract

The palladium-catalyzed aqueous α-arylation of ketones was developed and tested for a large variety of reaction partners. These mild conditions enabled the coupling of aryl/ alkyl-ketones with N-protected halotryptophans, heterocyclic haloarenes, and challenging base-sensitive compounds. The synthetic potential of this new methodology for the diversification of complex bioactive molecules was exemplified by derivatising prochlorperazine. The methodology is mild, aqueous and flexible, representing a means of functionalizing a wide range of halo-aromatics and therefore has the potential to be extended to complex molecule diversification.
Close

Details

Original languageEnglish
Pages (from-to)3832-3836
Number of pages5
JournalChemistry - A European Journal
Volume23
Issue number16
Early online date6 Mar 2017
DOIs
StatePublished - 17 Mar 2017

    Research areas

  • Palladium, Aqueous coupling, Halogenated compounds, Ketone arylation, Amino acids

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. Living GenoChemetics by hyphenating synthetic biology and synthetic chemistry in vivo

    Sharma, S. V., Tong, X., Pubill-Ulldemolins, C., Cartmell, C., Bogosyan, E. J. A., Rackham, E. J., Marelli, E., Hamed, R. B. & Goss, R. J. M. 9 Aug 2017 In : Nature Communications. 8, 10 p., 229

    Research output: Contribution to journalArticle

  2. Short and sweet: Pac13 is a small, monomeric dehydratase that mediates the formation of the 3′- deoxy nucleoside of pacidamycins

    Michailidou, F., Chung, C., Brown, M., Bent, A. F., Naismith, J. H., Leavens, W., Lynn, S., Sharma, S. V. & Goss, R. J. M. 8 Aug 2017 In : Angewandte Chemie.

    Research output: Contribution to journalArticle

  3. Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water

    Corr, M. J., Sharma, S. V., Pubill Ulldemolins, C., Bown, R. T., Poirot, P., Smith, D. R. M., Cartmell, C., Abou Fayad, A. & Goss, R. J. M. 1 Mar 2017 In : Chemical Science. 8, 3, p. 2039-2046 8 p.

    Research output: Contribution to journalArticle

  4. Rapid enzyme regeneration results in the striking catalytic longevity of an engineered, single species, biocatalytic biofilm

    Tong, X., Barberi, T. T., Botting, C. H., Sharma, S. V., Simmons, M. J. H., Overton, T. W. & Goss, R. J. M. 21 Oct 2016 In : Microbial Cell Factories. 15, 1, 11 p., 180

    Research output: Contribution to journalArticle

  5. A one-pot synthesis of symmetrical and unsymmetrical dipeptide ureas

    Abou Fayad, A., Pubill Ulldemolins, C., Sharma, S. V., Day, D. & Goss, R. J. M. Sep 2015 In : European Journal of Organic Chemistry. 25, p. 5603-5609 8 p.

    Research output: Contribution to journalArticle

Related by journal

  1. The synthesis and evaluation of fluoro-, trifluoromethyl, and iodomuscimols as GABA agonists

    Abdul Manan, M. A. F., Cordes, D., Slawin, A., Buehl, M., Liao, V., Chua, H., Chebib, M. & O'Hagan, D. 10 Aug 2017 In : Chemistry - A European Journal. 23, 45, p. 10848-10852 5 p.

    Research output: Contribution to journalArticle

  2. Multimetallic and mixed environment iridium(III) complexes: a modular approach to luminescence tuning using a host platform

    Pritchard, V. E., Rota Martir, D., Zysman-Colman, E. & Hardie, M. J. 3 Jul 2017 In : Chemistry - A European Journal. 23, 37, p. 8839-8849 11 p.

    Research output: Contribution to journalArticle

  3. Solid-state NMR spectroscopy proves the presence of penta-coordinated Sc sites in MIL-100(Sc)

    Giovine, R., Volkringer, C., Ashbrook, S. E., Trébosc, J., McKay, D., Loiseau, T., Amoureux, J-P., Lafon, O. & Pourpoint, F. 24 May 2017 In : Chemistry - A European Journal. Early View

    Research output: Contribution to journalArticle

  4. Highly electron rich β-diketiminato systems: synthesis and coordination chemistry of amino functionalized "N-nacnac" ligands

    Do, D. C. H., Keyser, A., Protchenko, A. V., Maitland, B., Pernik, I., Niu, H., Kolychev, E. L., Rit, A., Vidovic, D., Stasch, A., Jones, C. & Aldridge, S. 27 Apr 2017 In : Chemistry - A European Journal. 23, 24, p. 5830-5841 11 p.

    Research output: Contribution to journalArticle

  5. Homochiral self-sorted and emissive IrIII metallo-cryptophanes

    Pritchard, V. E., Rota Martir, D., Oldknow, S., Kai, S., Hiraoka, S., Cookson, N. J., Zysman-Colman, E. & Hardie, M. J. 20 Apr 2017 In : Chemistry - A European Journal. Early View

    Research output: Contribution to journalArticle

Related by journal

  1. Chemistry - A European Journal (Journal)

    Stuart John Conway (Editor)
    2007 → …

    Activity: Publication peer-review and editorial workEditor of research journal

ID: 249163299