Reaction of Dioxazolones with Boronic Acids: Copper-Mediated Synthesis of <i>N</i>-Aryl Amides via <i>N</i>-Acyl Nitrenes

Abstract

Dioxazolones, as direct amide sources, have been used with boronic acids in the presence of copper(I) chloride to access <i>N</i>-aryl amides at room temperature. The versatility of the developed reaction is proven by ample scope having a wide range of functional group tolerance. The reaction optimization conditions revealed that a fluorine additive demonstrated improved reactivity toward the intended transformation. The addition of triphenylphosphine resulted in <i>N</i>-acyl iminophosphorane, suggesting the involvement of an <i>N</i>-acyl nitrene intermediate.