Copper‐Catalyzed C─N Cross‐Coupling of Benzohydrazides with Boronic Acids for N ‐Aryl Amide Synthesis

ABSTRACT

An operationally simple and efficient protocol for the synthesis of N ‐aryl amides has been developed, based on the copper‐catalyzed coupling of benzohydrazides with boronic acids. The transformation relies on the unique in situ activation of the benzohydrazide precursors using a telescoped mixture of tert ‐butyl nitrite (TBN) and trimethylsilyl chloride (TMSCl). The subsequent cross‐coupling process is efficiently promoted by copper(I) chloride, potassium tert ‐butoxide, and cesium fluoride (CsF) under open‐air, ambient‐temperature conditions. Furthermore, this one‐pot protocol enables rapid access to a broad range of 27 examples of N ‐aryl amide derivatives, delivering moderate to excellent yields ranging from 40% to 88% under mild conditions with excellent functional group tolerance. The operational simplicity, ambient open‐air conditions, demonstrated synthetic utility, and gram‐scale applicability underscore the practical value of this protocol.