Reductive Dimerization of Azides to Secondary Amines under Hydrogenation Conditions

摘要

The catalytic hydrogenation of organic functional groups such as imine,nitrile,oxime,azide,nitro,and nitroso into the corresponding amines is a fundamental organic transformation.In the course of our study on the synthesis of polyamines,we used the catalytic hydrogenation for the conversion of a simple azide compound into the corresponding primary amine.We found that a significant amount of an unknown product was always accompanied along with the desired amine depending on reaction conditions.The unknown product was identified to be a secondary amine,which was produced through a "reductive dimerization" process(Equation 1).