Stannylene cyanide and its use as a cyanosilylation catalyst.

Two routes can offer the first stannylene cyanide [(L)SnCN] (5); the substitution reaction of either stannylene amide [(-Bu)ATISnN(SiMe)] (3) or stannylene pyrrolide [(-Bu)ATISn(NCH)] (4) using an excess of trimethylsilyl cyanide (L = aminotroponiminate (ATI)). Using 0.1-2.0 mol% of compound 5, catalytic cyanosilylation of a variety of aliphatic and aromatic aldehydes was achieved at rt-50 °C in 0.33-2.0 h. The mechanism of this catalytic reaction is authenticated by the isolation of a structurally characterized intermediate.