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Practical Azidation of 1,3-Dicarbonyls

Authors

  • Tobias Harschneck,

    1. Department of Chemistry, Technische Universität München, Lichtenbergstr. 4, 85747 Garching (Germany), Fax: (+49) 8928913315
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  • Sara Hummel,

    1. Department of Chemistry, Technische Universität München, Lichtenbergstr. 4, 85747 Garching (Germany), Fax: (+49) 8928913315
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  • Prof. Dr. Stefan F. Kirsch,

    Corresponding author
    1. Department of Chemistry, Technische Universität München, Lichtenbergstr. 4, 85747 Garching (Germany), Fax: (+49) 8928913315
    2. Fachbereich C-Organic Chemistry, Bergische Universität Wuppertal, Gaußstraße 20, 42119 Wuppertal (Germany)
    • Department of Chemistry, Technische Universität München, Lichtenbergstr. 4, 85747 Garching (Germany), Fax: (+49) 8928913315
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  • Philipp Klahn

    1. Department of Chemistry, Technische Universität München, Lichtenbergstr. 4, 85747 Garching (Germany), Fax: (+49) 8928913315
    2. Fachbereich C-Organic Chemistry, Bergische Universität Wuppertal, Gaußstraße 20, 42119 Wuppertal (Germany)
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Abstract

An operationally simple, direct azidation of 1,3-dicarbonyl compounds has been developed. The reaction proceeds readily under ambient conditions using sodium azide and an iodine-based oxidant such as I2 or 2-iodoxybenzoic acid (IBX)-SO3K/NaI. In particular, the latter method, as a new and well-balanced oxidizing agent, shows excellent functional group tolerance and substrate scope and thus allows access to a variety of tertiary 2-azido and 2,2-bisazido 1,3-dicarbonyl compounds that would be more difficult to access by using traditional methods. Because the azide-containing products easily undergo 1,3-dipolar cycloaddition with alkynes, our report represents a novel route to analogues of sensitive complex molecules.

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