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Water-promoted C-S bond formation reactions

Author

Listed:
  • Peizhong Xie

    (Nanjing Tech University)

  • Jinyu Wang

    (Nanjing Tech University)

  • Yanan Liu

    (Nanjing Tech University)

  • Jing Fan

    (Nanjing Tech University)

  • Xiangyang Wo

    (Nanjing Tech University)

  • Weishan Fu

    (Nanjing Tech University)

  • Zuolian Sun

    (Nanjing Tech University)

  • Teck-Peng Loh

    (Nanjing Tech University
    Nanyang Technological University)

Abstract

Allylic sulfones, owning to their widespread distributions in biologically active molecules, received increasing attention in the past few years. However, the synthetic method under mild conditions is still a challenging task. In this paper, we report a sulfinic acids ligation with allylic alcohols via metal-free dehydrative cross-coupling. Both aliphatic and aromatic sulfinic acids react with various allylic alcohols to deliver the desired allylic sulfones in high yields with excellent selectivity. This carbon–sulfur bond formation reaction is highly efficient and practical since it works under metal-free, neutral, aqueous media and at room temperature in which the products even can be obtained by simple filtration without the need for organic extraction or column chromatography. Water is found to be essential for the success of this carbon–sulfur bond formation reaction. DFT calculations imply that water acts as promoter in this transformation via intermolecular hydrogen bonds.

Suggested Citation

  • Peizhong Xie & Jinyu Wang & Yanan Liu & Jing Fan & Xiangyang Wo & Weishan Fu & Zuolian Sun & Teck-Peng Loh, 2018. "Water-promoted C-S bond formation reactions," Nature Communications, Nature, vol. 9(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-03698-8
    DOI: 10.1038/s41467-018-03698-8
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