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Concurrent Biocatalytic Oxidation and C–C Bond Formation via Gold Catalysis: One-Pot Alkynylation of N-Alkyl Tetrahydroisoquinolines

  • Marcin Odachowski
    Marcin Odachowski
    School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, United Kingdom
    School of Chemistry, University of Manchester, Manchester Institute of Biotechnology, 131 Princess Street, Manchester M1 7DN, United Kingdom
    More by Marcin Odachowski
  • , 
  • Michael F. Greaney*
    Michael F. Greaney
    School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, United Kingdom
    *E-mail for M.F.G.: [email protected]
    More by Michael F. Greaney
    Orcidhttp://orcid.org/0000-0001-9633-1135
  • , and 
  • Nicholas J. Turner*
    Nicholas J. Turner
    School of Chemistry, University of Manchester, Manchester Institute of Biotechnology, 131 Princess Street, Manchester M1 7DN, United Kingdom
    *E-mail for N.J.T.: [email protected]
    More by Nicholas J. Turner
    Orcidhttp://orcid.org/0000-0002-8708-0781
Cite this: ACS Catal. 2018, 8, 11, 10032–10035
Publication Date (Web):September 21, 2018
https://doi.org/10.1021/acscatal.8b03169
Copyright © 2018 American Chemical Society
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    Abstract

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    A cross-dehydrogenative coupling process has been developed involving the enzymatic oxidation of tetrahydroisoquinolines (THIQ) together with gold-catalyzed C–C bond-formation. The transformation demonstrates the compatibility of gold-mediated chemocatalysis and monoamine oxidase biocatalysis which act co-operatively in one vessel. A range of N-alkyl THIQs were functionalized in this manner at C-(1) position in high yields.

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