REDUCTION OF AMIDES AND SILYL ESTERS WITH TRICHLOROSILANE-TERT-AMINES

It is demonstrated that the trichlorosilane-t-amine combination is capable of reducing aromatic tertiary amides. As is customary in such reductions, the carbonyl moiety of the amide grouping is replaced by the elements of H⋯SiCl2. The intermediates in these reductions have been identified and characterized. A one-pot, two step synthesis has been developed for reducing aromatic tertiary amides to the corresponding benzylamines. Unexpectedly, aromatic esters proved resistants to reduction by tichlorosilane-t-amine, despite the fact that aromatic acids are readily reduced. On the other hand, silicon esters reduce with remarkable ease. The reason for the dramatic differences in rate of reduction of these carbonyl derivatives is not understood. © 1979.