Authors:	Bieneck, Jessica C. Mashtakov, Boris Schollmeyer, Dieter Waldvogel, Siegfried R.
Title:	Dehydrogenative electrochemical synthesis of N-aryl-3,4-dihydroquinolin-2-ones by iodine(III)-mediated coupling reaction
Online publication date:	15-Dec-2023
Year of first publication:	2023
Language:	english
Abstract:	Electrochemically generated hypervalent iodine(III) species are powerful reagents for oxidative C-N coupling reactions, providing access to valuable N-heterocycles. A new electrocatalytic hypervalent iodine(III)-mediated in-cell synthesis of 1H-N-aryl-3,4-dihydroquinolin-2-ones by dehydrogenative C-N bond formation is presented. Catalytic amounts of the redox mediator, a low supporting electrolyte concentration and recycling of the solvent used make this method a sustainable alternative to electrochemical ex-cell or conventional approaches. Furthermore, inexpensive, readily available electrode materials and a simple galvanostatic set-up are applied. The broad functional group tolerance could be demonstrated by synthesizing 23 examples in yields up to 96%, with one reaction being performed on a 10-fold higher scale. Based on the obtained results a sound reaction mechanism could be proposed.
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-9756
Version:	Published version
Publication type:	Zeitschriftenaufsatz
License:	CC BY
Information on rights of use:	https://creativecommons.org/licenses/by/4.0/
Journal:	Annalen der Physik Version of Record (VoR)
Pages or article number:	e202303388
Publisher:	Wiley-VCH
Publisher place:	Berlin
Issue date:	2023
ISSN:	1521-3889
Publisher DOI:	10.1002/chem.202303388
Appears in collections:	DFG-491381577-H