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

Author

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  • 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
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    References listed on IDEAS

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    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.
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