IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-30320-9.html
   My bibliography  Save this article

Parts–per–million of ruthenium catalyze the selective chain–walking reaction of terminal alkenes

Author

Listed:
  • Sergio Sanz-Navarro

    (Universidad Politècnica de València–Consejo Superior de Investigaciones Científicas, Avda. de los Naranjos s/n)

  • Marta Mon

    (Universidad Politècnica de València–Consejo Superior de Investigaciones Científicas, Avda. de los Naranjos s/n)

  • Antonio Doménech-Carbó

    (Universitat de Valencia, Dr Moliner, 50)

  • Rossella Greco

    (Universidad Politècnica de València–Consejo Superior de Investigaciones Científicas, Avda. de los Naranjos s/n)

  • Jorge Sánchez-Quesada

    (International Flavours & Fragrances Inc., Avda Felipe Klein 2)

  • Estela Espinós-Ferri

    (International Flavours & Fragrances Inc., Avda Felipe Klein 2)

  • Antonio Leyva-Pérez

    (Universidad Politècnica de València–Consejo Superior de Investigaciones Científicas, Avda. de los Naranjos s/n)

Abstract

The chain–walking of terminal alkenes (also called migration or isomerization reaction) is currently carried out in industry with unselective and relatively costly processes, to give mixtures of alkenes with significant amounts of oligomerized, branched and reduced by–products. Here, it is shown that part–per–million amounts of a variety of commercially available and in–house made ruthenium compounds, supported or not, transform into an extremely active catalyst for the regioselective migration of terminal alkenes to internal positions, with yields and selectivity up to >99% and without any solvent, ligand, additive or protecting atmosphere required, but only heating at temperatures >150 °C. The resulting internal alkene can be prepared in kilogram quantities, ready to be used in nine different organic reactions without any further treatment.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30320-9
    DOI: 10.1038/s41467-022-30320-9
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-30320-9
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-022-30320-9?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. Francisco Juliá-Hernández & Toni Moragas & Josep Cornella & Ruben Martin, 2017. "Remote carboxylation of halogenated aliphatic hydrocarbons with carbon dioxide," Nature, Nature, vol. 545(7652), pages 84-88, May.
    2. Tian-Sheng Mei & Harshkumar H. Patel & Matthew S. Sigman, 2014. "Enantioselective construction of remote quaternary stereocentres," Nature, Nature, vol. 508(7496), pages 340-344, April.
    3. 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)

    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. 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.
    2. Fan-Tao Meng & Ya-Nan Wang & Xiao-Yan Qin & Shi-Jun Li & Jing Li & Wen-Juan Hao & Shu-Jiang Tu & Yu Lan & Bo Jiang, 2022. "Azoarene activation for Schmidt-type reaction and mechanistic insights," Nature Communications, Nature, vol. 13(1), pages 1-12, December.
    3. Dongquan Zhang & Miaomiao Li & Jiajia Li & Aijun Lin & Hequan Yao, 2021. "Rhodium-catalyzed intermolecular enantioselective Alder–ene type reaction of cyclopentenes with silylacetylenes," Nature Communications, Nature, vol. 12(1), pages 1-7, 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_s41467-022-30320-9. 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.