A facile preparation of N-heterocyclic olefins: ring-opening polymerization of β-butyrolactone and frustrated Lewis pair reactivity

A direct synthesis of N-heterocyclic olefins (NHOs) and their mesoionic congeners from N-hererocyclic carbenes and N-aziridinylimines is reported. The reaction provided diverse functionalized (m)NHOs and π-extended analogues. The prepared NHOs initiated the ring-opening polymerization of β-butyrolactone, and insertion of aldehyde and nitrile into a NHO–B(C6F5)3 adduct was demonstrated.