IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-31617-5.html
   My bibliography  Save this article

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

Author

Listed:
  • 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
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-31617-5
    File Function: Abstract
    Download Restriction: no

    File URL: https://libkey.io/10.1038/s41467-022-31617-5?utm_source=ideas
    LibKey link: if access is restricted and if your library uses this service, LibKey will redirect you to where you can use your library subscription to access this item
    ---><---

    References listed on IDEAS

    as
    1. Jiahui Xue & Xuefeng Jiang, 2020. "Unsymmetrical polysulfidation via designed bilateral disulfurating reagents," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    2. 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.
    3. 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.
    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.
    Full references (including those not matched with items on IDEAS)

    Most related items

    These are the items that most often cite the same works as this one and are cited by the same works as this one.
    1. 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.
    2. 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.
    3. Long Huang & Tengfei Ji & Chen Zhu & Huifeng Yue & Nursaya Zhumabay & Magnus Rueping, 2022. "Bioinspired desaturation of alcohols enabled by photoredox proton-coupled electron transfer and cobalt dual catalysis," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    4. Guanghao Ji & Xinqiang Chen & Jing Zhang, 2024. "Direct ketone synthesis from primary alcohols and alkenes enabled by a dual photo/cobalt catalysis," Nature Communications, Nature, vol. 15(1), pages 1-8, December.

    More about this item

    Statistics

    Access and download statistics

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31617-5. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    If CitEc recognized a bibliographic reference but did not link an item in RePEc to it, you can help with this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Sonal Shukla or Springer Nature Abstracting and Indexing (email available below). General contact details of provider: http://www.nature.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.