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Tuning Chemoselectivity in Iron-Catalyzed Sonogashira-Type Reactions Using a Bisphosphine Ligand with Peripheral Steric Bulk: Selective Alkynylation of Nonactivated Alkyl Halides

Authors

  • Dr. Takuji Hatakeyama,

    1. International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011 (Japan)
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  • Yoshihiro Okada,

    1. International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011 (Japan)
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  • Yuya Yoshimoto,

    1. International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011 (Japan)
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  • Prof. Masaharu Nakamura

    Corresponding author
    1. International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011 (Japan)
    • International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011 (Japan)
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  • This work is granted by the Japan Society for the Promotion of Science (JSPS) through the “Funding Program for Next Generation World-Leading Researchers (NEXT Program),” initiated by the Council for Science and Technology Policy (CSTP). Financial support from Tosoh Finechem Corporations, the Noguchi Institute, and a Grant-in-Aid for Scientific Research on Innovative Areas “Integrated Organic Synthesis” is also acknowledged.

Abstract

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Sterisch abgeschirmt: Der Eisen-Phosphan-Komplex 1 vermittelt eine hoch Cmath image-selektive Alkinylierung nichtaktivierter Alkylhalogenide mit entsprechenden Grignard-Reagentien. Primäre und sekundäre Alkyliodide, -bromide und -chloride liefern in guten Ausbeuten die substituierten Alkine, die anschließend Cyclisierungen und Kreuzkupplungen eingehen können.

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