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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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The incredible bulk: A highly Cmath image-center-selective alkynylation of nonactivated alkyl halides with the corresponding Grignard reagents is achieved by using the iron-phosphine complex 1. Primary and secondary alkyl iodides, bromides, and chlorides take part in the reaction to give the substituted alkynes in good to excellent yields. Sequential cyclization/cross-coupling reactions are also demonstrated.

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