N-Silylamines in catalysis: synthesis and reactivity

Abstract

A summary of the catalytic synthesis and reactivity of N-silylated amines is presented. Dehydrocoupling of amines with silanes, hydrosilylation of imines and dealkenylative coupling of amines with vinylsilanes are three ways to achieve their catalytic syntheses. The resultant N-silylamines serve as substrates in a variety of reactions, including C–N and C–C bond forming reactions, and are preferred in transformations because of the facile Si–N hydrolytic cleavage to reveal free amine products upon reaction completion. This review highlights the distinct electronic properties of N-silyl amines, N-silyl imines and N-silyl enamines that result in complementary reactivity to that of parent non-silyl variants.