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1,2,4- and 1,3,4-Oxadiazole Synthesis by Palladium-Catalyzed Carbonylative Assembly of Aryl Bromides with Amidoximes or Hydrazides

Authors

  • Thomas L. Andersen,

    1. Center for Insoluble Protein Structures, Center for Interdisciplinary Nanoscience, Department of Chemistry, Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
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  • Wiliam Caneschi,

    1. Center for Insoluble Protein Structures, Center for Interdisciplinary Nanoscience, Department of Chemistry, Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
    2. Department of Chemistry, Federal University of Juiz de Fora, Campus Martelos, Juiz de Fora, MG 36036-330, Brazil
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  • Ali Ayoub,

    1. Center for Insoluble Protein Structures, Center for Interdisciplinary Nanoscience, Department of Chemistry, Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
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  • Anders T. Lindhardt,

    Corresponding author
    1. Center for Interdisciplinary Nanoscience, Biological and Chemical Engineering, Department of Engineering, Aarhus University, Finlandsgade 22, 8200 Aarhus N, Denmark
    • Anders T. Lindhardt, Center for Interdisciplinary Nanoscience, Biological and Chemical Engineering, Department of Engineering, Aarhus University, Finlandsgade 22, 8200 Aarhus N, Denmark

      Troels Skrydstrup, Center for Insoluble Protein Structures, Center for Interdisciplinary Nanoscience, Department of Chemistry, Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark

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  • Mara R. C. Couri,

    1. Department of Chemistry, Federal University of Juiz de Fora, Campus Martelos, Juiz de Fora, MG 36036-330, Brazil
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  • Troels Skrydstrup

    Corresponding author
    1. Center for Insoluble Protein Structures, Center for Interdisciplinary Nanoscience, Department of Chemistry, Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
    • Anders T. Lindhardt, Center for Interdisciplinary Nanoscience, Biological and Chemical Engineering, Department of Engineering, Aarhus University, Finlandsgade 22, 8200 Aarhus N, Denmark

      Troels Skrydstrup, Center for Insoluble Protein Structures, Center for Interdisciplinary Nanoscience, Department of Chemistry, Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark

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Abstract

Aryl bromides were successfully transformed into their corresponding N,N′-diacylhydrazines via a Pd-catalyzed carbonylative coupling with acylhydrazines. These reactions employed near-stoichiometric amounts of carbon monoxide generated ex situ from a non-gaseous precursor. A range of di(hetero)aryl diacylhydrazines was isolated in good to excellent yields. Furthermore, dehydration conditions were identified that could be used in a compatible one-pot synthesis of 1,3,4-oxadiazoles. The applicability of this method towards 13C-isotope labeling was also demonstrated, with the production of symmetrical and non-symmetrical doubly isotopically labeled 1,3,4-oxadiazoles. Finally, experimental conditions were identified for the carbonylative coupling of aryl bromides with amidoximes and CO producing 1,2,4-oxadiazoles after spontaneous dehydration.

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