Visible-light-driven palladium-catalyzed Dowd-Beckwith ring expansion/C-C bond formation cascade

A visible-light-induced palladium-catalyzed Dowd-Beckwith ring expansion/C-C bond formation cascade is described. A range of six to nine-membered beta-alkenylated cyclic ketones possessing a quaternary carbon center were accessed under mild conditions. Besides styrenes, the electron-rich alkenes such as silyl enol ethers and enamides were also compatible, providing the desired beta-alkylated cyclic ketones in moderate to good yields.

Automated summary

A visible light-induced palladium-catalyzed Dowd-Beckwith ring expansion/C-C bond formation cascade has been successfully developed to access a variety of six to nine-membered beta-alkenylated cyclic ketones with a quaternary carbon center under mild conditions. In addition to styrenes, electron-rich alkenes like silyl enol ethers and enamides are also compatible substrates, providing the desired beta-alkylated cyclic ketones in moderate to good yields.