Issue 10, 2024

E-Dakin reaction: oxidation of hydroxybenzaldehydes to phenols with electrochemically generated peroxodicarbonate as sustainable ex-cell oxidizer

Abstract

Electrochemically generated peroxodicarbonate solution efficiently oxidizes hydroxybenzaldehydes to valuable phenols. The reaction is carried out in aqueous media without additional solvents or additives. The reaction gives high yields of up to 97% and tolerates a broad variety of substituents, as demonstrated by 20 diverse examples. It was successfully scaled to multi-gram range. This transformation further expands the synthetic applicability of the green oxidizer peroxodicarbonate, which can be generated on demand from ecologically safe carbonate solutions and has a high oxidation potential at mildly basic conditions.

Graphical abstract: E-Dakin reaction: oxidation of hydroxybenzaldehydes to phenols with electrochemically generated peroxodicarbonate as sustainable ex-cell oxidizer

Supplementary files

Article information

Article type
Paper
Submitted
24 Nov 2023
Accepted
08 Feb 2024
First published
08 Feb 2024
This article is Open Access
Creative Commons BY license

Green Chem., 2024,26, 5862-5868

E-Dakin reaction: oxidation of hydroxybenzaldehydes to phenols with electrochemically generated peroxodicarbonate as sustainable ex-cell oxidizer

F. Sprang, N. Schupp, P. J. Kohlpaintner, L. J. Gooßen and S. R. Waldvogel, Green Chem., 2024, 26, 5862 DOI: 10.1039/D3GC04597H

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