Dehydrogenative Electrochemical Synthesis of N‐Aryl‐3,4‐Dihydroquinolin‐2‐ones by Iodine(III)‐Mediated Coupling Reaction
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Abstract
- <jats:title>Abstract</jats:title><jats:p>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 1<jats:italic>H</jats:italic>‐<jats:italic>N</jats:italic>‐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.</jats:p>
- Autoren
- Jessica C Bieniek
- Boris Mashtakov
- Dieter Schollmeyer
- Siegfried R Waldvogel
- DOI
- 10.1002/chem.202303388
- eISSN
- 1521-3765
- ISSN
- 0947-6539
- Ausgabe der Veröffentlichung
- 7
- Zeitschrift
- Chemistry – A European Journal
- Sprache
- en
- Online publication date
- 2023
- Datum der Veröffentlichung
- 2024
- Status
- Published
- Herausgeber
- Wiley
- Herausgeber URL
- http://dx.doi.org/10.1002/chem.202303388
- Datum der Datenerfassung
- 2024
- Titel
- Dehydrogenative Electrochemical Synthesis of <i>N</i>‐Aryl‐3,4‐Dihydroquinolin‐2‐ones by Iodine(III)‐Mediated Coupling Reaction
- Ausgabe der Zeitschrift
- 30
Datenquelle: Crossref
- Andere Metadatenquellen:
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- Author's licence
- CC-BY
- Autoren
- Jessica C Bieneck
- Boris Mashtakov
- Dieter Schollmeyer
- Siegfried R Waldvogel
- Hosting institution
- Universitätsbibliothek Mainz
- Sammlungen
- DFG-491381577-H
- Resource version
- Published version
- DOI
- 10.1002/chem.202303388
- File(s) embargoed
- false
- Open access
- true
- ISSN
- 1521-3889
- Zeitschrift
- Annalen der Physik
- Schlüsselwörter
- 540 Chemie
- 540 Chemistry and allied sciences
- Sprache
- eng
- Open access status
- Open Access
- Paginierung
- e202303388
- Datum der Veröffentlichung
- 2023
- Public URL
- https://openscience.ub.uni-mainz.de/handle/20.500.12030/9774
- Herausgeber
- Wiley-VCH
- Datum der Datenerfassung
- 2023
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2023
- Zugang
- Public
- Titel
- Dehydrogenative electrochemical synthesis of N-aryl-3,4-dihydroquinolin-2-ones by iodine(III)-mediated coupling reaction
- Ausgabe der Zeitschrift
- Version of Record (VoR)
Files
primer_on_axion_physics-20231215101856215.pdf
Datenquelle: OPENSCIENCE.UB