Access to Secondary Amines Through Hydrogen Autotransfer Reaction Mediated by KOtBu

We report herein an N-alkylation reaction of amines with alcohols through a hydrogen autotransfer reaction. Unlike other catalytic systems containing transition metals or additives, potassium tertiary butoxide was found to be a unique and effective catalyst for synthesizing secondary amines. The role of the K+ ion and the reaction intermediates were studied under control experiments and by theoretical calculations. The reaction was found to be general and tolerates a series of functional groups, providing a convenient method to synthesize N-alkylated compounds.