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Catalyst-Free N-Arylation Using Unactivated Fluorobenzenes

Authors

  • Dr. Frederik Diness,

    Corresponding author
    1. Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland, Brisbane, Queensland 4072 (Australia)
    2. Current address: Department of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen (Denmark)
    • Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland, Brisbane, Queensland 4072 (Australia)
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  • Prof. David P. Fairlie

    Corresponding author
    1. Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland, Brisbane, Queensland 4072 (Australia)
    • Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland, Brisbane, Queensland 4072 (Australia)
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  • We acknowledge the Carlsberg Foundation (Denmark) for a postdoctoral fellowship (to F.D.) and the Australian Research Council and NHMRC for fellowships (to D.P.F.).

Abstract

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Caught in a ‘SNAr'e: A one-step, high-yielding, catalyst-free method is described for N-arylation of azoles and indoles from unactivated monofluorobenzenes. This SNAr reaction tolerates a wide range of substituents and can also generate halogenated N-aryl products. The reaction can also be performed simultaneously with or subsequent to a copper- or palladium-catalyzed cross-coupling reaction in the same pot.

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