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Unsymmetrical polysulfidation via designed bilateral disulfurating reagents

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  • Jiahui Xue

    (East China Normal University)

  • Xuefeng Jiang

    (East China Normal University
    Chinese Academy of Sciences
    Nankai University)

Abstract

Sulfur-sulfur motifs widely occur in vital function and drug design, which yearns for polysulfide construction in an efficient manner. However, it is a great challenge to install desired functional groups on both sides of sulfur-sulfur bonds at liberty. Herein, we designed a mesocyclic bilateral disulfurating reagent for sequential assembly and modular installation of polysulfides. Based on S-O bond dissociation energy imparity (mesocyclic compared to linear imparity is at least 5.34 kcal mol−1 higher), diverse types of functional molecules can be bridged via sulfur-sulfur bonds distinctly. With these stable reagents, excellent reactivities with nucleophiles including C, N and S are comprehensively demonstrated, sequentially installing on both sides of sulfur-sulfur motif with various substituents to afford six species of unsymmetrical polysulfides including di-, tri- and even tetra-sulfides. Life-related molecules, natural products and pharmaceuticals can be successively cross-linked with sulfur-sulfur bond. Remarkably, the cyclization of tri- and tetra-peptides affords 15- and 18-membered cyclic disulfide peptides with this reagent, respectively.

Suggested Citation

  • Jiahui Xue & Xuefeng Jiang, 2020. "Unsymmetrical polysulfidation via designed bilateral disulfurating reagents," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-18029-z
    DOI: 10.1038/s41467-020-18029-z
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    Cited by:

    1. Ziqian Bai & Shiyang Zhu & Yiyao Hu & Peng Yang & Xin Chu & Gang He & Hao Wang & Gong Chen, 2022. "Synthesis of N-acyl sulfenamides via copper catalysis and their use as S-sulfenylating reagents of thiols," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    2. 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.
    3. Hengzhao Li & Mengqi Peng & Junyu Li & Lijun Wang & Hainam Do & Ke Ni & Minlong Wang & Zhankui Yuan & Tianxiao Zhao & Xiaohe Zhang & Xiaoxu Zhang & Zhaonong Hu & Fazheng Ren & Jie An, 2024. "SO2F2 mediated click chemistry enables modular disulfide formation in diverse reaction media," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    4. Jingjing Zhang & Armido Studer, 2022. "Decatungstate-catalyzed radical disulfuration through direct C-H functionalization for the preparation of unsymmetrical disulfides," Nature Communications, Nature, vol. 13(1), pages 1-8, December.

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