Authors:	Nikl, Joachim Hofman, Kamil Mossazghi, Samuel Möller, Isabel C. Mondeshki, Daniel Weinelt, Frank Baumann, Franz-Erich Waldvogel, Siegfried R.
Title:	Electrochemical oxo-functionalization of cyclic alkanes and alkenes using nitrate and oxygen
Online publication date:	30-Nov-2023
Year of first publication:	2023
Language:	english
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.
DDC:	540 Chemie 540 Chemistry and allied sciences
Institution:	Johannes Gutenberg-Universität Mainz
Department:	FB 09 Chemie, Pharmazie u. Geowissensch.
Place:	Mainz
ROR:	https://ror.org/023b0x485
DOI:	http://doi.org/10.25358/openscience-9726
Version:	Published version
Publication type:	Zeitschriftenaufsatz
Document type specification:	Scientific article
License:	CC BY
Information on rights of use:	https://creativecommons.org/licenses/by/4.0/
Journal:	Nature Communications 14
Pages or article number:	4565
Publisher:	Springer Nature
Publisher place:	London
Issue date:	2023
ISSN:	2041-1723
Publisher DOI:	10.1038/s41467-023-40259-0
Appears in collections:	DFG-491381577-G