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Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes

Author

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  • Xiaoli Jiang

    (Nanjing University)

  • Bo Han

    (Nanjing University)

  • Yuhang Xue

    (Nanjing University)

  • Mei Duan

    (Nanjing University)

  • Zhuofan Gui

    (Nanjing University)

  • You Wang

    (Nanjing University)

  • Shaolin Zhu

    (Nanjing University)

Abstract

α-Chiral alkyne is a key structural element of many bioactive compounds, chemical probes, and functional materials, and is a valuable synthon in organic synthesis. Here we report a NiH-catalysed reductive migratory hydroalkynylation of olefins with bromoalkynes that delivers the corresponding benzylic alkynylation products in high yields with excellent regioselectivities. Catalytic enantioselective hydroalkynylation of styrenes has also been realized using a simple chiral PyrOx ligand. The obtained enantioenriched benzylic alkynes are versatile synthetic intermediates and can be readily transformed into synthetically useful chiral synthons.

Suggested Citation

  • Xiaoli Jiang & Bo Han & Yuhang Xue & Mei Duan & Zhuofan Gui & You Wang & Shaolin Zhu, 2021. "Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes," Nature Communications, Nature, vol. 12(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-24094-9
    DOI: 10.1038/s41467-021-24094-9
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    Cited by:

    1. Yao Zhang & Deyong Qiao & Mei Duan & You Wang & Shaolin Zhu, 2022. "Enantioselective synthesis of α-aminoboronates by NiH-catalysed asymmetric hydroamidation of alkenyl boronates," Nature Communications, Nature, vol. 13(1), pages 1-8, December.

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