The iridium-catalyzed oxidative coupling and cyclization of NH isoquinolones with olefins has been realized. Most isoindolo[2,1-b]isoquinolin-5(7H)-one derivatives were obtained in moderate to good yields. Several derivatization reactions including functional group conversion and further C-H/olefin coupling were also performed. This transformation realized the less developed Cp*Ir(III) catalyzed coupling and cyclization reaction of NH substrates with olefins. (c) 2022 Elsevier Ltd. All rights reserved.