Sodium bis(trimethylsilyl)amide in the oxidative conversion of aldehydes to nitriles

Abstract

The feasibility of the Me3Si species acting as a nucleofuge was investigated in compounds containing the NSiMe3 moiety. Treatment of various aromatic aldehydes with 2.2 equiv. of NaN(SiMe3)2 at 185°C in a sealed tube produced the corresponding nitriles in high yields (81-98%). In these reactions, NaN(SiMe3)2 acted as an oxidizing agent. Results from control experiments indicate that the Me 3Si unit can depart efficiently from the NSiMe3 moiety of N-silylimine intermediates. © Wiley-VCH Verlag GmbH & Co. KGaA, 2006.