Synthesis, Isolation, and Characterization of Mono- and Bis-norbornene-Annulated Biarylamines through Pseudo-Catellani Intermediates

A palladium-catalyzed C–H functionalization of an external ring of N-acyl 2-aminobiaryl with bicyclo[2.2.1]­hept-2-ene (norbornene) via multiple C–H bond activations was developed. This study is the first report of the formation of bis-norbornene annulated biarylamines isomers (syn-3a′/anti-3a′ = 36:64) from multiple C–H bond functionalizations. Additionally, nondirected C–H bond functionalization at the C-4′ position with alkenes rendered complete C–H functionalization of five C–H bonds that formed a stable hexasubstituted benzene ring.