Direct Oxidative Allylic and Vinylic Amination of Alkenes through Selenium Catalysis

Authors

  • M. Sc. Johanna Trenner,

    1. Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany)
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  • B. Sc. Christian Depken,

    1. Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany)
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  • B. Sc. Thomas Weber,

    1. Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany)
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  • Dr. Alexander Breder

    Corresponding author
    1. Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany)
    • Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen (Germany)===

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  • This work was financially supported by the Fonds der Chemischen Industrie (Liebig fellowship to A.B.). We thank Prof. Dr. Lutz Ackermann for generous support of our work. We thank Stefan Ortgies and Hauke Stürznickel for preparing several substrates.

Abstract

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Bringing “N” into the game: The direct chemoselective nitrogenation of unactivated alkenes can be achieved through oxidative selenium catalysis (see scheme). This method provides a broad variety of allylic imides in yields of up to 89 % using N-fluorobenzenesulfonimide (NFSI) as the terminal oxidant and nitrogen source. Furthermore, an unprecedented selenium-catalyzed vinylic C(sp2)–H nitrogenation was discovered.

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