Dehydrogenative Electrochemical Synthesis of N ‐Aryl‐3,4‐Dihydroquinolin‐2‐ones by Iodine (III)‐Mediated Coupling Reaction

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.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Dehydrogenative Electrochemical Synthesis of N ‐Aryl‐3,4‐Dihydroquinolin‐2‐ones by Iodine (III)‐Mediated Coupling Reaction ; day:13 ; month:12 ; year:2023 ; extent:9 ; Chemistry - a European journal ; (13.12.2023) (gesamt 9)

Contributors, Places and Time

• Creator: Bieniek, Jessica C. ; Mashtakov, Boris ; Schollmeyer, Dieter ; Waldvogel, Siegfried R.

Further information

• DOI: 10.1002/chem.202303388
• URN: urn:nbn:de:101:1-2023121414132737440346
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 15.08.2025, 7:39 AM CEST