Radical Cascade Annulation of Biphenyl Acrylamides to Dibenzoazepinones: Experimental and DFT Studies

Abstract An efficient method for the conversion of biphenyl acrylamides to dibenzoazepinones with −SCF 3 incorporation is described. This operationally simple radical cascade reaction employs CAN as an oxidant and exhibits good functional group tolerance. Substrates featuring −OCH 3 , −CH 3 , −Br or −Cl at the para ‐position of the aromatic ring exhibits a preference for an ipso ‐cyclization due to the intervention of DMSO in the reaction. Density functional theory (DFT) calculations provide valuable insights into the reaction's energetics and product selectivity.