Stannylene cyanide and its use as a cyanosilylation catalyst

Abstract

Two routes can offer the first stannylene cyanide [(L)SnCN] (5); the substitution reaction of either stannylene amide [(i-Bu)₂ATISnN(SiMe₃)₂] (3) or stannylene pyrrolide [(i-Bu)₂ATISn(NC₄H₄)] (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.