IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v16y2025i1d10.1038_s41467-025-56681-5.html
   My bibliography  Save this article

Catalytic transformation of carbon dioxide into seven-membered heterocycles and their domino transformation into bicyclic oxazolidinones

Author

Listed:
  • Wangyu Shi

    (Institute of Chemical Research of Catalonia (ICIQ-Cerca)
    C/Marcel·lí Domingo s/n)

  • Jordi Benet-Buchholz

    (Institute of Chemical Research of Catalonia (ICIQ-Cerca))

  • Arjan W. Kleij

    (Institute of Chemical Research of Catalonia (ICIQ-Cerca)
    Catalan Institute of Research and Advanced Studies (ICREA))

Abstract

Converting carbon dioxide (CO2) into valuable heterocycles is of great synthetic value but is usually limited to five- and six-membered ring compounds. Here, we report a catalytic approach for transforming this carbon renewable into seven-membered heterocycles using a double-stage approach, combining a silver-catalyzed alkyne/CO2 coupling and a subsequent base-catalyzed ring-expansion. This methodology avoids the formation of thermodynamically more stable, smaller-ring by-products and has good functional group tolerance. The synthetic application of these larger-ring cyclic carbonates is further demonstrated by showing their unique ability to serve as synthons for the preparation of bicyclic oxazolidinone pharmacores through an intramolecular domino sequence that involves a transient ketimine group, and various other intermolecular transformations. The results described herein significantly expand on the use of CO2 as a cheap and versatile carbon feedstock generating elusive heterocycles and pharmaceutically relevant compounds.

Suggested Citation

  • Wangyu Shi & Jordi Benet-Buchholz & Arjan W. Kleij, 2025. "Catalytic transformation of carbon dioxide into seven-membered heterocycles and their domino transformation into bicyclic oxazolidinones," Nature Communications, Nature, vol. 16(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-56681-5
    DOI: 10.1038/s41467-025-56681-5
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-025-56681-5
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-025-56681-5?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. Qiang Liu & Lipeng Wu & Ralf Jackstell & Matthias Beller, 2015. "Using carbon dioxide as a building block in organic synthesis," Nature Communications, Nature, vol. 6(1), pages 1-15, May.
    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. Yu Zhang & Jaro Vanderghinste & Jinxin Wang & Shoubhik Das, 2024. "Challenges and recent advancements in the synthesis of α,α-disubstituted α-amino acids," Nature Communications, Nature, vol. 15(1), pages 1-18, December.
    2. Yushu Jin & Joaquim Caner & Shintaro Nishikawa & Naoyuki Toriumi & Nobuharu Iwasawa, 2022. "Catalytic direct hydrocarboxylation of styrenes with CO2 and H2," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    3. Anja Hansen & Jörn Budde & Yusuf Nadi Karatay & Annette Prochnow, 2016. "CUDe —Carbon Utilization Degree as an Indicator for Sustainable Biomass Use," Sustainability, MDPI, vol. 8(10), pages 1-17, October.
    4. Rui Sang & Yuya Hu & Rauf Razzaq & Guillaume Mollaert & Hanan Atia & Ursula Bentrup & Muhammad Sharif & Helfried Neumann & Henrik Junge & Ralf Jackstell & Bert U. W. Maes & Matthias Beller, 2022. "A practical concept for catalytic carbonylations using carbon dioxide," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    5. Yuman Qin & Robin Cauwenbergh & Suman Pradhan & Rakesh Maiti & Philippe Franck & Shoubhik Das, 2023. "Straightforward synthesis of functionalized γ-Lactams using impure CO2 stream as the carbon source," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    6. Wei Zhang & Zhen Chen & Yuan-Xu Jiang & Li-Li Liao & Wei Wang & Jian-Heng Ye & Da-Gang Yu, 2023. "Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysis," Nature Communications, Nature, vol. 14(1), pages 1-10, 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:16:y:2025:i:1:d:10.1038_s41467-025-56681-5. 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.