Ruthenium-catalyzed dealkenative N-silylation of amines by substituted vinylsilanes

Dalton Trans. 2015 Jan 14;44(2):782-6. doi: 10.1039/c4dt03084b. Epub 2014 Nov 14.

Abstract

The ruthenium hydride complex-catalyzed N-silylation of primary and secondary amines with substituted vinylsilanes, with the general formula R(1)CH=CHSiR (where R(1) = H, Ph, n-Bu, Si(OEt)3), leading to the formation of a Si-N bond with the evolution of olefin is described. Vinylsilane acts as a silylative reagent and hydrogen acceptor. Under optimum conditions, the reaction offers an attractive route for the synthesis of silylamines. The preliminary mechanistic view of this novel general silylation reaction based on catalytic and deuterium labeling experiments, using NMR and GC-MS methods, confirm the synthetic observations.