Issue 2, 2015

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

Abstract

The ruthenium hydride complex-catalyzed N-silylation of primary and secondary amines with substituted vinylsilanes, with the general formula R1CH[double bond, length as m-dash]CHSiR3 (where R1 = 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.

Graphical abstract: Ruthenium-catalyzed dealkenative N-silylation of amines by substituted vinylsilanes

Supplementary files

Article information

Article type
Paper
Submitted
07 Oct 2014
Accepted
05 Nov 2014
First published
06 Nov 2014

Dalton Trans., 2015,44, 782-786

Author version available

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

B. Marciniec, S. Kostera, B. Wyrzykiewicz and P. Pawluć, Dalton Trans., 2015, 44, 782 DOI: 10.1039/C4DT03084B

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