Yu S, Xiong M, Xie X, Liu Y * Shanghai Institute of Organic Chemistry, P. R. of China
Insertion of Nitriles into Zirconocene 1-aza-1,3-diene Complexes: Chemoselective Synthesis
of N–H and N-Substituted Pyrroles.
Angew. Chem. Int. Ed. 2014;
53: 11596-11599
Key words
zirconium - nitriles - cyclization
Significance
Liu and co-workers report the direct insertion of nitriles into zirconocene-1-aza-1,3-diene
complexes for the synthesis of variously substituted N–H and N-substituted pyrroles
in high yields.
Comment
The outcome of the reaction is determined by different cyclization patterns that depend
on the relative stability and reactivity of the enamine–imine tautomers that are formed
upon hydrolysis of the diazazirconacycles.
