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Electrochemical oxo-functionalization of cyclic alkanes and alkenes using nitrate and oxygen

Author

Listed:
  • Joachim Nikl

    (Johannes Gutenberg University Mainz)

  • Kamil Hofman

    (Johannes Gutenberg University Mainz)

  • Samuel Mossazghi

    (Johannes Gutenberg University Mainz)

  • Isabel C. Möller

    (Johannes Gutenberg University Mainz)

  • Daniel Mondeshki

    (Johannes Gutenberg University Mainz)

  • Frank Weinelt

    (Evonik Operations GmbH)

  • Franz-Erich Baumann

    (Evonik Operations GmbH)

  • Siegfried R. Waldvogel

    (Johannes Gutenberg University Mainz)

Abstract

Direct functionalization of C(sp3)–H bonds allows rapid access to valuable products, starting from simple petrochemicals. However, the chemical transformation of non-activated methylene groups remains challenging for organic synthesis. Here, we report a general electrochemical method for the oxidation of C(sp3)–H and C(sp2)–H bonds, in which cyclic alkanes and (cyclic) olefins are converted into cycloaliphatic ketones as well as aliphatic (di)carboxylic acids. This resource-friendly method is based on nitrate salts in a dual role as anodic mediator and supporting electrolyte, which can be recovered and recycled. Reducing molecular oxygen as a cathodic counter reaction leads to efficient convergent use of both electrode reactions. By avoiding transition metals and chemical oxidizers, this protocol represents a sustainable oxo-functionalization method, leading to a valuable contribution for the sustainable conversion of petrochemical feedstocks into synthetically usable fine chemicals and commodities.

Suggested Citation

  • Joachim Nikl & Kamil Hofman & Samuel Mossazghi & Isabel C. Möller & Daniel Mondeshki & Frank Weinelt & Franz-Erich Baumann & Siegfried R. Waldvogel, 2023. "Electrochemical oxo-functionalization of cyclic alkanes and alkenes using nitrate and oxygen," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-40259-0
    DOI: 10.1038/s41467-023-40259-0
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    1. Meenakshisundaram Sankar & Ewa Nowicka & Emma Carter & Damien M. Murphy & David W. Knight & Donald Bethell & Graham J. Hutchings, 2014. "The benzaldehyde oxidation paradox explained by the interception of peroxy radical by benzyl alcohol," Nature Communications, Nature, vol. 5(1), pages 1-6, May.
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