IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-35293-3.html
   My bibliography  Save this article

Catalytic direct hydrocarboxylation of styrenes with CO2 and H2

Author

Listed:
  • Yushu Jin

    (Tokyo Institute of Technology, O-okayama, Meguro-ku)

  • Joaquim Caner

    (Tokyo Institute of Technology, O-okayama, Meguro-ku)

  • Shintaro Nishikawa

    (Tokyo Institute of Technology, O-okayama, Meguro-ku)

  • Naoyuki Toriumi

    (Tokyo Institute of Technology, O-okayama, Meguro-ku)

  • Nobuharu Iwasawa

    (Tokyo Institute of Technology, O-okayama, Meguro-ku)

Abstract

A three-component hydrocarboxylation of an olefin with CO2 and H2 could be regarded as a dream reaction, since it would provide a straightforward approach for the synthesis of aliphatic carboxylic acids in perfect atom economy. However, this transformation has not been realized in a direct manner under mild conditions, because boosting the carboxylation with thermodynamically stable CO2 while suppressing the rapid hydrogenation of olefin remains a challenging task. Here, we report a rhodium-catalysed reductive hydrocarboxylation of styrene derivatives with CO2 and H2 under mild conditions, in which H2 served as the terminal reductant. In this approach, the carboxylation process was largely accelerated by visible light irradiation, which was proved both experimentally and by computational studies. Hydrocarboxylation of various kinds of styrene derivatives was achieved in good yields without additional base under ambient pressure of CO2/H2 at room temperature. Mechanistic investigations revealed that use of a cationic rhodium complex was critical to achieve high hydrocarboxylation selectivity.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-35293-3
    DOI: 10.1038/s41467-022-35293-3
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-35293-3
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-022-35293-3?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.
    2. Lipeng Wu & Qiang Liu & Ivana Fleischer & Ralf Jackstell & Matthias Beller, 2014. "Ruthenium-catalysed alkoxycarbonylation of alkenes with carbon dioxide," Nature Communications, Nature, vol. 5(1), pages 1-6, May.
    Full references (including those not matched with items on IDEAS)

    Citations

    Citations are extracted by the CitEc Project, subscribe to its RSS feed for this item.
    as


    Cited by:

    1. 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.

    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. 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.
    2. 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.
    3. 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.
    4. 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.
    5. 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.
    6. Sergio Sanz-Navarro & Marta Mon & Antonio Doménech-Carbó & Rossella Greco & Jorge Sánchez-Quesada & Estela Espinós-Ferri & Antonio Leyva-Pérez, 2022. "Parts–per–million of ruthenium catalyze the selective chain–walking reaction of terminal alkenes," Nature Communications, Nature, vol. 13(1), pages 1-9, 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_s41467-022-35293-3. 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.