Aldehydes and Imines into Metal-Carbon Bonds

Insertions of Aldehydes and Imines into Metal-Carbon Bonds 

The insertions of imines into late transition metal-carbon bonds are even less common. In one case, the insertion of an imine into Ni- and Pd-acyl bonds occurs with 2,1-regiochemistry to form an aminoalkyl product (Equation 9.80). Tlus reaction is likely to occur through a polar transition state formed by attack of a nucleophilic nitrogen at the electrophilic acyl carbon. One set of examples of 1,2-insertions of imines into late metal-carbon bonds have been reported. This example involves insertion of N-aryl aldimines into rhodium-aryl complexes containing a labile pyridine ligand (Equation 9.81). The rates of these reactions were inverse order in added pyridine, suggesting that the reaction occurs by an intramolecular migratory insertion mechanism after replacement of the coordinated pyridine by the imine. 

Insertions of Olefins and Acetylenes into Metal-Heteroatom Bonds 

---