Palladium-Catalyzed [5+2] Rollover Annulation of 1-Benzylpyrazoles with Alkynes: A Direct Entry to Tricyclic 2-Benzazepines

The first Pd-catalyzed [5 + 2] rollover annulation of 1-benzylpyrazoles with alkynes to assemble 10H-benzo[e]pyrazolo-[1,5-a]azepines (tricyclic 2-benzazepines) has been developed. The rollover annulation implies a twofold C-H activation of aryl and heteroaryl C-sp(2)-H bonds (C-H/C-H) of 1-benzylpyrazoles (five-atom partners) and alkynes to give the [5 + 2] annulated compounds.

Automated summary

The first Pd-catalyzed [5 + 2] rollover annulation of 1-benzylpyrazoles with alkynes has been developed to assemble 10H-benzo[e]pyrazolo-[1,5-a]azepines (tricyclic 2-benzazepines). The rollover annulation involves twofold C-H activation of aryl and heteroaryl C-sp(2)-H bonds (C-H/C-H) of 1-benzylpyrazoles (five-atom partners) and alkynes, resulting in [5 + 2] annulated compounds.