Gutenberg Open Science: Metal-free electrochemical synthesis of sulfonamides directly from (hetero)arenes, SO2, and amines

Please use this identifier to cite or link to this item: http://doi.org/10.25358/openscience-6008

Full metadata record

DC Field	Value	Language
dc.contributor.author	Blum, Stephan P.	-
dc.contributor.author	Karakaya, Tarik	-
dc.contributor.author	Schollmeyer, Dieter	-
dc.contributor.author	Klapars, Artis	-
dc.contributor.author	Waldvogel, Siegfried R.	-
dc.date.accessioned	2021-06-22T08:22:17Z	-
dc.date.available	2021-06-22T08:22:17Z	-
dc.date.issued	2021	-
dc.identifier.uri	https://openscience.ub.uni-mainz.de/handle/20.500.12030/6017	-
dc.description.abstract	Sulfonamides are among the most important chemical motifs in pharmaceuticals and agrochemicals. However, there is no methodology to directly introduce the sulfonamide group to a non-prefunctionalized aromatic compound. Herein, we present the first dehydrogenative electrochemical sulfonamide synthesis protocol by exploiting the inherent reactivity of (hetero)arenes in a highly convergent reaction with SO2 and amines via amidosulfinate intermediate. The amidosulfinate serves a dual role as reactant and supporting electrolyte. Direct anodic oxidation of the aromatic compound triggers the reaction, followed by nucleophilic attack of the amidosulfinate. Boron-doped diamond (BDD) electrodes and a HFIP–MeCN solvent mixture enable selective formation of the sulfonamides. In total, 36 examples are demonstrated with yields 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	Metal-free electrochemical synthesis of sulfonamides directly from (hetero)arenes, SO2, and amines	en_GB
dc.type	Zeitschriftenaufsatz	de
dc.identifier.doi	http://doi.org/10.25358/openscience-6008	-
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	Angewandte Chemie	de
jgu.journal.volume	60	de
jgu.journal.issue	10	de
jgu.pages.start	5056	de
jgu.pages.end	5062	de
jgu.publisher.year	2021	-
jgu.publisher.name	Wiley-VCH	de
jgu.publisher.place	Weinheim	de
jgu.publisher.uri	https://doi.org/10.1002/anie.202016164	de
jgu.publisher.issn	1521-3773	de
jgu.organisation.place	Mainz	-
jgu.subject.ddccode	540	de
jgu.publisher.doi	10.1002/anie.202016164	-
jgu.organisation.ror	https://ror.org/023b0x485	-
Appears in collections:	JGU-Publikationen

Files in This Item:

	File	Description	Size	Format
	blum_stephan_p.-metal-free_ele-20210607143716399.pdf		2.56 MB	Adobe PDF	View/Open

Show simple item record