Gutenberg Open Science: Optimization strategies for the anodic phenol-arene cross-coupling reaction

Please use this identifier to cite or link to this item: http://doi.org/10.25358/openscience-8031

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DC Field	Value	Language
dc.contributor.author	Hielscher, Maximilian	-
dc.contributor.author	Oehl, Elisabeth K.	-
dc.contributor.author	Gleede, Barbara	-
dc.contributor.author	Buchholz, Julian	-
dc.contributor.author	Waldvogel, Siegfried R.	-
dc.date.accessioned	2022-10-25T09:24:22Z	-
dc.date.available	2022-10-25T09:24:22Z	-
dc.date.issued	2021	-
dc.identifier.uri	https://openscience.ub.uni-mainz.de/handle/20.500.12030/8046	-
dc.description.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 %.	en_GB
dc.language.iso	eng	de
dc.rights	CC BY-NC-ND	*
dc.rights.uri	https://creativecommons.org/licenses/by-nc-nd/4.0/	*
dc.subject.ddc	540 Chemie	de_DE
dc.subject.ddc	540 Chemistry and allied sciences	en_GB
dc.title	Optimization strategies for the anodic phenol-arene cross-coupling reaction	en_GB
dc.type	Zeitschriftenaufsatz	de
dc.identifier.doi	http://doi.org/10.25358/openscience-8031	-
jgu.type.dinitype	article	en_GB
jgu.type.version	Published version	de
jgu.type.resource	Text	de
jgu.organisation.department	FB 09 Chemie, Pharmazie u. Geowissensch.	de
jgu.organisation.number	7950	-
jgu.organisation.name	Johannes Gutenberg-Universität Mainz	-
jgu.rights.accessrights	openAccess	-
jgu.journal.title	ChemElectroChem	de
jgu.journal.volume	8	de
jgu.journal.issue	20	de
jgu.pages.start	3904	de
jgu.pages.end	3910	de
jgu.publisher.year	2021	-
jgu.publisher.name	Wiley-VCH	de
jgu.publisher.place	Weinheim	de
jgu.publisher.issn	2196-0216	de
jgu.organisation.place	Mainz	-
jgu.subject.ddccode	540	de
jgu.publisher.doi	10.1002/celc.202101226	de
jgu.organisation.ror	https://ror.org/023b0x485	-
Appears in collections:	JGU-Publikationen

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