Palladium-Catalysed Amide-Directed Ligand Free C8-Olefination of 1-Naphthamides for the synthesis of 2,3-dihydro-1H-benzo[de]isoquinolin-1-ones

This work describes the palladium(II)-catalyzed regioselective C8-H olefination of 1-naphthamides. Interestingly, naphthamide fused lactam 2,3-dihydro-1H-benzo[de]isoquinolin-1-one derivatives were also synthesized in the case of a particular class of napthamides. This protocol was found well compatible with a diverse range of acrylates and styrenes leading to product formation in good yields along with a wide functional group tolerance. The developed strategy was further applied to the synthesis of different drug derivatives.

Automated summary

This work presents a palladium(II)-catalyzed regioselective C8-H olefination of 1-naphthamides. Notably, naphthamide fused lactam 2,3-dihydro-1H-benzo[de]isoquinolin-1-one derivatives were synthesized in a particular class of napthamides. The reaction showed good compatibility with a diverse range of acrylates and styrenes, providing the desired products with high yields and tolerance to various functional groups. The developed strategy was further employed for the synthesis of different drug derivatives.