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Nickel-catalysed selective migratory hydrothiolation of alkenes and alkynes with thiols

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  • Yulong Zhang

    (Nanjing University)

  • Xianfeng Xu

    (Nanjing University)

  • Shaolin Zhu

    (Nanjing University
    Chinese Academy of Sciences)

Abstract

Direct (utilize easily available and abundant precursors) and selective (both chemo- and regio-) aliphatic C–H functionalization is an attractive mean with which to streamline chemical synthesis. With many possible sites of reaction, traditional methods often need an adjacent polar directing group nearby to achieve high regio- and chemoselectivity and are often restricted to a single site of functionalization. Here we report a remote aliphatic C–H thiolation process with predictable and switchable regioselectivity through NiH-catalysed migratory hydrothiolation of two feedstock chemicals (alkenes/alkynes and thiols). This mild reaction avoids the preparation of electrophilic thiolation reagents and is highly selective to thiols over other nucleophilic groups, such as alcohols, acids, amines, and amides. Mechanistic studies show that the reaction occurs through the formation of an RS-Bpin intermediate, and THF as the solvent plays an important role in the regeneration of NiH species.

Suggested Citation

  • Yulong Zhang & Xianfeng Xu & Shaolin Zhu, 2019. "Nickel-catalysed selective migratory hydrothiolation of alkenes and alkynes with thiols," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-09783-w
    DOI: 10.1038/s41467-019-09783-w
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    Cited by:

    1. Jiale Ying & Yan Tan & Zhan Lu, 2024. "Cobalt-catalyzed hydrothiolation of alkynes for the diverse synthesis of branched alkenyl sulfides," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    2. Daning Zeng & Zihao Liu & Guoce Huang & You Wang & Shaolin Zhu, 2024. "Regio-, stereo-, and enantioselective ipso- and migratory defluorinative olefin cross-coupling to access highly functionalized monofluoroalkenes," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    3. 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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