High yielding electrophilic amination with lower order and higher order organocuprates: Application of acetone O-(4-Chlorophenylsulfonyl)oxime in the construction of the C−N bond at room temperature

Abstract

Electrophilic amination reaction was performed with lower order and higher order organocuprates using acetone O-(4-Chlorophenylsulfonyl)oxime (1). It was proceeded smoothly at room temperature in the presence of organocuprates to provide the corresponding primary amines in good yields with 10 and 60 min, respectively. The primary amine yields of the electrophilic amination of bromomagnesium organocyanocuprates and dibromomagnesium diorganocyanocuprates were obtained 52–72% and 58–83%, respectively. We observed that higher order organocuprates were more successful than lower order organocuprates in the synthesis of functionalized arylamines by electrophilic amination.