Autoren:	Bieneck, Jessica C. Mashtakov, Boris Schollmeyer, Dieter Waldvogel, Siegfried R.
Titel:	Dehydrogenative electrochemical synthesis of N-aryl-3,4-dihydroquinolin-2-ones by iodine(III)-mediated coupling reaction
Online-Publikationsdatum:	15-Dez-2023
Erscheinungsdatum:	2023
Sprache des Dokuments:	Englisch
Zusammenfassung/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-Sachgruppe:	540 Chemie 540 Chemistry and allied sciences
Veröffentlichende Institution:	Johannes Gutenberg-Universität Mainz
Organisationseinheit:	FB 09 Chemie, Pharmazie u. Geowissensch.
Veröffentlichungsort:	Mainz
ROR:	https://ror.org/023b0x485
DOI:	http://doi.org/10.25358/openscience-9756
Version:	Published version
Publikationstyp:	Zeitschriftenaufsatz
Nutzungsrechte:	CC BY
Informationen zu den Nutzungsrechten:	https://creativecommons.org/licenses/by/4.0/
Zeitschrift:	Annalen der Physik Version of Record (VoR)
Seitenzahl oder Artikelnummer:	e202303388
Verlag:	Wiley-VCH
Verlagsort:	Berlin
Erscheinungsdatum:	2023
ISSN:	1521-3889
DOI der Originalveröffentlichung:	10.1002/chem.202303388
Enthalten in den Sammlungen:	DFG-491381577-H