Copper(I)-Mediated Decarboxylative N-Arylation of Dioxazolones: Synthesis of N-Aryl Amides

Abstract

Dioxazolones, which are potent amide precursors, have been widely explored for the formation of C–N bonds with the help of transition-metal catalysts. Here, we highlight our recent studies on the synthesis of N-aryl amides using dioxazolones and boronic acids in the presence of copper(I) chloride under mild conditions. The versatility of the developed reaction is demonstrated by its wide range of functional-group tolerances as well as the release of nontoxic carbon dioxide. Optimization screenings reveal that a fluorine additive improves the desired reactivity toward the intended transformation. The addition of triphenylphosphine results in an N-acyl iminophosphorane, suggesting the involvement of an N-acyl nitrene intermediate in this transformation.