Perfluorinated pinacol promotes efficient amidination of 2-aminophenylboronic acid

Abstract

This work reports the use of halogenated alcohols in catalyzing a unique amidination reaction using 2-aminophenylboronic acid. Trials using acetonitrile as the reactant nitrile showed that the amidination efficiency increased from 33% with salicylic acid, to 78% with 2,2,2-trifluoroethanol and finally quantitative yields with perfluorinated pinacol. This protecting group proved to be highly efficient for amidination of several different nitrile groups with only mild heating.