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Cobalt-catalyzed hydrothiolation of alkynes for the diverse synthesis of branched alkenyl sulfides

Author

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  • Jiale Ying

    (Zhejiang University)

  • Yan Tan

    (Zhengzhou University)

  • Zhan Lu

    (Zhejiang University
    Zhengzhou University)

Abstract

Alkenyl sulfides have gained increasing prominence in medicinal chemistry and materials. Hydrothiolation of alkynes for the diverse synthesis of alkenyl sulfides is an appealing method. Herein, we report a cobalt-catalyzed Markovnikov hydromethylthiolation of alkynes to afford branched alkenyl methylsulfanes with good yields and high regioselectivity. This method also enables the diverse synthesis of branched alkenyl sulfides. The reaction shows good functional group tolerance and could be scaled up. The mechanistic studies including control experiments, deuterium-labeling experiments, and Hammett plot indicated alkynes insertion followed by electrophilic thiolation pathway.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-52249-x
    DOI: 10.1038/s41467-024-52249-x
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    References listed on IDEAS

    as
    1. Jieping Chen & Jiale Ying & Zhan Lu, 2022. "Cobalt-catalyzed branched selective hydroallylation of terminal alkynes," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    2. 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.
    3. Yi Fang & Torben Rogge & Lutz Ackermann & Shun-Yi Wang & Shun-Jun Ji, 2018. "Nickel-catalyzed reductive thiolation and selenylation of unactivated alkyl bromides," Nature Communications, Nature, vol. 9(1), pages 1-10, December.
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