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Silylative reduction of nitriles was studied under transition metal-free conditions by using B(C6F5)3 as a catalyst with hydrosilanes as a reductant. Alkyl and (hetero)aryl nitriles were efficiently converted to primary amines or imines under mild conditions. The choice of silanes was found to determine the selectivity: while a full reduction of nitriles was highly facile, the use of sterically bulky silanes allowed for the partial reduction leading to N-silylimines.

The B(C6F5)3-catalyzed silylative reduction of conjugated nitriles has been developed to afford synthetically valuable β-silyl amines. The reaction is chemoselective and proceeds under mild conditions. Mechanistic elucidation indicates that it proceeds by rapid double hydrosilylation of the conjugated nitrile to an enamine intermediate which is subsequently reduced to the β-silyl amine, thus forming a new C(sp3)Si bond. Based on this mechanistic understanding, a preparative route to enamines was also established using bulky silanes. [ABSTRACT FROM AUTHOR]

In the presence of excess diphenyl and triphenyl silane acryl nitriles are reduced to silyl amines and N-disilyl enamines. [ABSTRACT FROM AUTHOR]

Silylative reduction of nitriles is performed under transition metal-free conditions by using B(C6F5)3 as a catalyst with hydrosilanes as a reductant. [ABSTRACT FROM AUTHOR]