Nickel-catalyzed CN bond formation of diarylamine between nitroarenes and aryl Grignard reagents

Abstract

In recent years, transition-metal-catalyzed CN bond formation from nitroarenes and aryl Grignard reagents has emerged as a promising and highly efficient method. Despite this, dinitro aromatic compounds have received limited attention in this context. Herein, we disclose a novel approach for synthesizing diarylamines via Ni-catalyzed cross-coupling of Grignard reagents with both mono- and di-nitro aromatic compounds. This method demonstrates remarkable tolerance towards a wide range of functional groups, including COOEt, F, Cl, CN, CF₃, OCF₃, SCH₃, and pyridyl groups, allowing for the synthesis of various aminated arenes in moderate to good yields. This CN bond formation method offers a general and step-economical pathway to diaryl and polyaryl amines, paving the way for new synthetic possibilities.