Hydroxylamine for the Transition-Metal-Free Amination Reaction

Hydroxylamine-O-sulfonic acid (HSA, 1) is utilized in amination reaction of benzene moieties. 1 behaves as an amino cation equivalent and affords primary anilines in high yields by the treatment of phenylboronic acid derivatives at room temperature under basic conditions. This reaction is applicable to not only the substances with electron-donating groups but also those with electron-withdrawing groups. Furthermore, this reaction proceeds without any transition metals. 1 is expected to be used as a tool for the easier preparation of anilines.