α-Silyl amines as electron donors: application in synthetic organic chemistry

α-Silyl amines are unique organosilicon compounds containing a geminal NCH 2 Si fragment. The introduction of a triorganylsilyl group at α-position to the nitrogen atom decreases the ionization potential and promotes an electron transfer with the formation of the corresponding radical cation. The review discusses methods for generating α-silyl amine radical cations (electrochemical, chemical, and photochemical) and also generalizes and systematizes reactions of α-silyl amines which include the stage of single-electron transfer. Single-electron oxidation of neutral α-silyl amines is a simple and efficient approach to highly reactive C-centered α-aminoalkyl radicals, which are very attractive from the point of view of synthetic organic chemistry in terms of the formation of new carbon—carbon bonds.