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Authors: Hielscher, Maximilian
Oehl, Elisabeth K.
Gleede, Barbara
Buchholz, Julian
Waldvogel, Siegfried R.
Title: Optimization strategies for the anodic phenol-arene cross-coupling reaction
Online publication date: 25-Oct-2022
Year of first publication: 2021
Language: english
Abstract: Dehydrogenative phenol-arene cross-coupling by direct anodic oxidation is a promising alternative to reductive cross-coupling, especially for construction of smaller molecules. The reaction pathway via phenoxyl radicals allows for unusual regioselectivity. Nevertheless, the numerous electrolysis parameters pose a challenge for optimization, as they determine the yield and selectivity of the reaction. Using design of experiments, we present optimization strategies for two example reactions to improve the space-time yield. In particular, coupling reactions with 2,6-dimethoxyphenol (syringol) were found to be very robust in the electrolysis at high current densities of up to 150 mA/cm2. Cyclic voltammetry was used to classify combinations of phenols and arenes, on the basis of which the various clusters were optimized. Based on this classification, various biaryls were synthesized and isolated in yields of up to 85 %.
DDC: 540 Chemie
540 Chemistry and allied sciences
Institution: Johannes Gutenberg-Universität Mainz
Department: FB 09 Chemie, Pharmazie u. Geowissensch.
Place: Mainz
Version: Published version
Publication type: Zeitschriftenaufsatz
License: CC BY-NC-ND
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Journal: ChemElectroChem
Pages or article number: 3904
Publisher: Wiley-VCH
Publisher place: Weinheim
Issue date: 2021
ISSN: 2196-0216
Publisher DOI: 10.1002/celc.202101226
Appears in collections:JGU-Publikationen

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