Photoinduced radical cascade domino Heck coupling of N-aryl acrylamide with vinyl arenes enabled by palladium catalysis

Here, a redox-neutral palladium-catalyzed photo-induced radical cascade domino Heck reaction of N-aryl acrylamide with vinyl arenes is described. A diverse range of bioactive oxindoles, featuring an all-carbon quaternary center, were synthesized. The reaction is proposed to proceed via an open-shell intermediate and occurs under mild reaction conditions, exhibiting excellent functional group tolerance. Importantly, the synthesized products can be readily transformed into biologically active molecules, including (& PLUSMN;)-physostigmine and (& PLUSMN;)-physovenine.

Automated summary

Described here is a redox-neutral palladium-catalyzed photo-induced radical cascade domino Heck reaction between N-aryl acrylamide and vinyl arenes. A variety of bioactive oxindoles with an all-carbon quaternary center were synthesized. The reaction proceeds via an open-shell intermediate and occurs under mild reaction conditions, showing excellent functional group tolerance. Importantly, the synthesized products can be readily transformed into biologically active molecules, including (& PLUSMN;)-physostigmine and (& PLUSMN;)-physovenine.