Herein, we describe a DBU/O2-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.
Athawale, Paresh R.,Kalmode, Hanuman P.,Reddy, D. Srinivasa
p. 9200 - 9205
(2021/07/19)
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