A unified approach to the synthesis of amines through a highly selective and broadly applicable imine reduction using modified Pd-nanoparticles

Abstract

A remarkably broad range of substrates is facilitated in a highly selective imine reduction using PVP stabilised Pd nanoparticles, molecular hydrogen at 1 atm, at just above RT in aqueous ethanol. Very good yields are achieved across previously-problematic substrate classes, and the protocol circumvents issues associated with more popular synthetic approaches. The utility of this system was further demonstrated in the context of late-stage functionalisation of APIs, deuterium incorporation and one-pot multi-step reaction sequences. Through a combination of synthetic mechanistic studies, surface analysis and computational approximations, insights into the features governing the selectivity of this system, and the key binding interactions between the PVP and Pd surface have been gleaned.