Unconventional Reactivity of a Grubbs Catalyst: Hydroalkylation Overriding Metathesis

Unprecedented reactivity of a Grubbs catalyst has been disclosed in a reaction between vinyl azaarenes and alkenylnitriles under standard metathesis conditions. No metathesis was observed; only hydroalkylation products were obtained in high yields. The practical utility of this method has been demonstrated by the application of the products in useful transformations, e.g., the formation of cyclic iminoesters and highly challenging medium-sized carbocycles.

Automated summary

This study reveals the unprecedented reactivity of a Grubbs catalyst in the reaction between vinyl azaarenes and alkenylnitriles under standard metathesis conditions, resulting in high-yield hydroalkylation products with no observed metathesis. The practical utility of the obtained products in useful transformations, such as the formation of cyclic iminoesters and highly challenging medium-sized carbocycles, has been demonstrated.