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Efficient preparation of unsymmetrical disulfides by nickel-catalyzed reductive coupling strategy

Author

Listed:
  • Fei Wang

    (Collaborative Innovation Center of Suzhou Nano Science and Technology Soochow University)

  • Ying Chen

    (Collaborative Innovation Center of Suzhou Nano Science and Technology Soochow University)

  • Weidong Rao

    (Nanjing Forestry University)

  • Lutz Ackermann

    (Institut für Organische und Biomolekulare Chemie Georg-August-Universität Göttingen Tammannstraße 2
    Wöhler Research Institute for Sustainable Chemistry Georg-August-Universität Göttingen Tammannstraße 2)

  • Shun-Yi Wang

    (Collaborative Innovation Center of Suzhou Nano Science and Technology Soochow University)

Abstract

Disulfides are widely found in natural products and find a wide range of applications in life sciences, materials chemistry and other fields. The preparation of disulfides mainly rely on oxidative couplings of two sulfur containing compounds. This strategy has many side reactions and other shortcomings. Herein, we describe the reductive nickel-catalyzed cross-electrophile coupling of unactivated alkyl bromides with symmetrical alkyl- and aryltetrasulfides to form alkyl-alkyl and aryl-alkyl unsymmetrical disulfides. This approach for disulfide synthesis is practical, relies on easily available, unfunctionalized substrates, and is scalable. We investigated the mechanism of this transformation and found that the tetrasulfide compound does not selectively break the central S–S bond, but regio-selectively generates trisulfide intermediates.

Suggested Citation

  • Fei Wang & Ying Chen & Weidong Rao & Lutz Ackermann & Shun-Yi Wang, 2022. "Efficient preparation of unsymmetrical disulfides by nickel-catalyzed reductive coupling strategy," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30256-0
    DOI: 10.1038/s41467-022-30256-0
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    References listed on IDEAS

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    1. Jiahui Xue & Xuefeng Jiang, 2020. "Unsymmetrical polysulfidation via designed bilateral disulfurating reagents," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    2. Xiao Xiao & Jiahui Xue & Xuefeng Jiang, 2018. "Polysulfurating reagent design for unsymmetrical polysulfide construction," Nature Communications, Nature, vol. 9(1), pages 1-9, December.
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