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Decatungstate-catalyzed radical disulfuration through direct C-H functionalization for the preparation of unsymmetrical disulfides

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  • Jingjing Zhang

    (Westfälische Wilhelms-Universität)

  • Armido Studer

    (Westfälische Wilhelms-Universität)

Abstract

Unsymmetrical disulfides are widely found in the areas of food chemistry, pharmaceutical industry, chemical biology and polymer science. Due the importance of such disulfides in various fields, general methods for the nondirected intermolecular disulfuration of C-H bonds are highly desirable. In this work, the conversion of aliphatic C(sp3)-H bonds and aldehydic C(sp2)-H bonds into the corresponding C-SS bonds with tetrasulfides (RSSSSR) as radical disulfuration reagents is reported. The decatungstate anion ([W10O32]4−) as photocatalyst is used for C-radical generation via intermolecular hydrogen atom transfer in combination with cheap sodium persulfate (Na2S2O8) as oxidant. Herein a series of valuable acyl alkyl disulfides, important precursors for the generation of RSS-anions, and unsymmetrical dialkyl disulfides are synthesized using this direct approach. To demonstrate the potential of the method for late-stage functionalization, approved drugs and natural products were successfully C-H functionalized.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31617-5
    DOI: 10.1038/s41467-022-31617-5
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    References listed on IDEAS

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    1. Julian G. West & David Huang & Erik J. Sorensen, 2015. "Acceptorless dehydrogenation of small molecules through cooperative base metal catalysis," Nature Communications, Nature, vol. 6(1), pages 1-7, December.
    2. Song Meng & Andrew D. Steele & Wei Yan & Guohui Pan & Edward Kalkreuter & Yu-Chen Liu & Zhengren Xu & Ben Shen, 2021. "Thiocysteine lyases as polyketide synthase domains installing hydropersulfide into natural products and a hydropersulfide methyltransferase," Nature Communications, Nature, vol. 12(1), pages 1-11, December.
    3. Jiahui Xue & Xuefeng Jiang, 2020. "Unsymmetrical polysulfidation via designed bilateral disulfurating reagents," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    4. 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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