Palladium-catalyzed carbonylative C–H activation of arenes with norbornene as the coupling partner

•The first study on carbonylative C–H activation and cyclization with alkene.•Applying molybdenum hexacarbonyl (Mo(CO)6) or paraformaldehyde as the solid CO sources.•Carbonylative synthesis of heterocycles.

An interesting transformation on palladium-catalyzed carbonylative C–H activation of arenes with norbornene as the coupling partner has been developed. By applying molybdenum hexacarbonyl (Mo(CO)6) or paraformaldehyde as the solid CO sources, various 5-(pyridin-2-yl)-hexahydro-7,10-methanophenanthridin-6(5H)-ones were produced in moderate yields in the presence of palladium catalyst. Interestingly, when DDQ was applied the oxidant, the product was over oxidized to the corresponding 5-(pyridin-2-yl)-tetrahydro-7,10-methanophenanthridin-6(5H)-one.

Graphical abstractAn interesting palladium-catalyzed carbonylative C–H activation of arenes with norbornene as the coupling partner has been developed. By applying Mo(CO)6 or paraformaldehyde as the solid CO sources, moderate yields of the desired products can be obtained.Figure optionsDownload full-size imageDownload as PowerPoint slide