Oxidative rearrangement of enaminones to α-keto amides in the presence of KI, TBHP and octanoic acid

Abstract

A novel method for the direct conversion of enaminones to α-keto amides has been developed. This transformation involves an oxidative rearrangement of enaminones under free radical conditions. In the presence of KI, TBHP and octanoic acid, a series of α-keto amides were obtained in moderate to excellent yields. This reaction demonstrates excellent functional group compatibility, utilizes readily available materials, and is easy to perform. Additionally, when o-hydroxyphenyl enaminone was utilized as the substrate, the reaction yielded 3-iodochromone in a high yield.