Base-Mediated Amination of Alcohols Using Amidines

Abstract

Novel and efficient base-mediated <i>N</i>-alkylation and amidation of amidines with alcohols have been developed, which can be carried out in one-pot reaction conditions, which allows for the synthesis of a wide range of <i>N</i>-alkyl amines and free amides in good to excellent yields with high atom economy. In contrast to borrowing hydrogen/hydrogen autotransfer or oxidative-type <i>N</i>-alkylation reactions, in which alcohols are activated by transition-metal-catalyzed or oxidative aerobic dehydrogenation, the use of amidines provides an effective surrogate of amines. This circumvents the inherent necessity in <i>N</i>-alkylation of an oxidant or a catalyst to be stabilized by ligands.