Samarium Borohydride as Effective Reagent for Synthesis of Various Imines and Secondary Amines

Abstract

A new and economical route for the oxidative homo-coupling of benzylamines with other aryl amines, and cross-coupling of benzyl alcohol and diverse arylamines to give respective imines with a high yield, and chemo-selectivity using samarium borohydride as the catalyst in a mild condition is reported. The sequential addition of samarium borohydride in a one-pot reaction to the imines generated in situ led to the generation of a number of secondary amines from the corresponding imines under elevated temperature. The use of samarium borohydride as a competent reagent for homo-coupling, cross-coupling, and the reduction of imines to secondary amine formation displayed a broad substrate scope. The reaction proceeded easily to afford the variously substituted imines, which eventually converted to secondary amines in yields that can be characterized as ranging between good and excellent.