IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v14y2023i1d10.1038_s41467-023-38748-3.html
   My bibliography  Save this article

Palladium-catalyzed regiodivergent hydrochlorocarbonylation of alkenes for formation of acid chlorides

Author

Listed:
  • Fei Wu

    (Northwest University)

  • Bo Wang

    (Northwest University)

  • Na-Qi Li

    (Northwest University)

  • Hui-Yi Yang

    (Northwest University)

  • Zhi-Hui Ren

    (Northwest University)

  • Zheng-Hui Guan

    (Northwest University)

Abstract

Novel strategy for acid chlorides formation that do not use carboxylic acids is particularly attractive in chemical synthesis but remains challenging. Herein, we reported the development of a highly effective Pd-catalyzed hydrochlorocarbonylation of alkenes with CO for the formation of alkyl acid chlorides. Chlorosilane and AcOH were found as a mild HCl source for the reaction. The reaction shows broad substrate scope and produces both branched and linear alkyl acid chlorides in good to high yields upon different ligands and solvents. Cooperating with follow-up acylation reactions, the Pd-catalyzed hydrochlorocarbonylation offers a complementary platform for the synthesis of diverse carbonyl compounds from alkenes. Mechanistic investigations suggested that the reaction proceeded though a palladium hydride pathway, and CO prompted reductive elimination of the acyl-Pd-Cl intermediate.

Suggested Citation

  • Fei Wu & Bo Wang & Na-Qi Li & Hui-Yi Yang & Zhi-Hui Ren & Zheng-Hui Guan, 2023. "Palladium-catalyzed regiodivergent hydrochlorocarbonylation of alkenes for formation of acid chlorides," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
  • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-38748-3
    DOI: 10.1038/s41467-023-38748-3
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-023-38748-3
    File Function: Abstract
    Download Restriction: no

    File URL: https://libkey.io/10.1038/s41467-023-38748-3?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. Qingyang Zhao & Le Yu & Yao-Du Zhang & Yong-Qiang Guo & Ming Chen & Zhi-Hui Ren & Zheng-Hui Guan, 2023. "C(alkyl)–C(vinyl) bond cleavage enabled by Retro-Pallada-Diels-Alder reaction," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    2. Kaiwu Dong & Xianjie Fang & Samet Gülak & Robert Franke & Anke Spannenberg & Helfried Neumann & Ralf Jackstell & Matthias Beller, 2017. "Highly active and efficient catalysts for alkoxycarbonylation of alkenes," Nature Communications, Nature, vol. 8(1), pages 1-7, April.
    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. Lei Su & Shen Gao & Jiawang Liu, 2024. "Enantioconvergent synthesis of axially chiral amides enabled by Pd-catalyzed dynamic kinetic asymmetric aminocarbonylation," Nature Communications, Nature, vol. 15(1), pages 1-14, 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. Kang Zhao & Hongli Wang & Teng Li & Shujuan Liu & Enrico Benassi & Xiao Li & Yao Yao & Xiaojun Wang & Xinjiang Cui & Feng Shi, 2024. "Identification of a potent palladium-aryldiphosphine catalytic system for high-performance carbonylation of alkenes," Nature Communications, Nature, vol. 15(1), pages 1-11, 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:14:y:2023:i:1:d:10.1038_s41467-023-38748-3. 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.