DBU/O-2-Mediated Oxidation of Dienones

DBU/O-2-Mediated Oxidation of Dienones

Herein, we describe a DBU/O-2-promoted novel method for oxidation of dienones to 2,6-dione derivatives. The reaction involves treatment of a dienone with DBU in acetonitrile employing molecular oxygen as the oxidant. Metal free conditions and an eco-friendly reagent are the striking features of this...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2021-07, Vol.86 (13), p.9200-9205
Hauptverfasser: Athawale, Paresh R., Kalmode, Hanuman P., Reddy, D. Srinivasa
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Herein, we describe a DBU/O-2-promoted novel method for oxidation of dienones to 2,6-dione derivatives. The reaction involves treatment of a dienone with DBU in acetonitrile employing molecular oxygen as the oxidant. Metal free conditions and an eco-friendly reagent are the striking features of this protocol. This transformation proceeds through a peroxide intermediate that upon Kornblum-DeLaMare rearrangement produces 2,6-diones. The method was successfully utilized for the synthesis of (+/-)-pleodendione with improved yields versus those of the traditional PDC-TBHP method.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00529