Authors:	Blum, Stephan P. Karakaya, Tarik Schollmeyer, Dieter Klapars, Artis Waldvogel, Siegfried R.
Title:	Metal-free electrochemical synthesis of sulfonamides directly from (hetero)arenes, SO2, and amines
Online publication date:	22-Jun-2021
Year of first publication:	2021
Language:	english
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 %.
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-6008
Version:	Published version
Publication type:	Zeitschriftenaufsatz
License:	CC BY-NC-ND
Information on rights of use:	https://creativecommons.org/licenses/by-nc-nd/4.0/
Journal:	Angewandte Chemie 60 10
Pages or article number:	5056 5062
Publisher:	Wiley-VCH
Publisher place:	Weinheim
Issue date:	2021
ISSN:	1521-3773
Publisher URL:	https://doi.org/10.1002/anie.202016164
Publisher DOI:	10.1002/anie.202016164
Appears in collections:	JGU-Publikationen