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

Joachim Nikl, Kamil Hofman, Samuel Mossazghi, Isabel C. Möller, Daniel Mondeshki, Frank Weinelt, Franz-Erich Baumann and Siegfried R. Waldvogel ()
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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

Nature Communications, 2023, vol. 14, issue 1, 1-11

Abstract: 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.

Date: 2023
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DOI: 10.1038/s41467-023-40259-0

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