Visible-Light-Promoted Selective Sulfonylation and Selenylation of Dienes to Access Sulfonyl-/Seleno-benzazepine Derivatives

A novelvisible-light-promoted selective sulfonylation and selenylationof dienes with selenosulfonates has been developed. This technologyprovides mild access to a wide range of sulfonyl benzo-[b]-azepinones and seleno-benzo-[b]-azepines. Preliminarymechanistic studies suggest that the sulfonylation involves a sulfonylradical engaged cascade process, and the selenylation is accomplishedthrough a sequential oxidation/electrophilic cyclization process.The large-scale operation and late-stage modification experiment revealthe promising utility of this protocol.

Automated summary

A novel visible-light-promoted selective sulfonylation and selenylation of dienes with selenosulfonates has been developed, providing mild access to a wide range of sulfonyl benzo-[b]-azepinones and seleno-benzo-[b]-azepines. Preliminary mechanistic studies suggest that the sulfonylation involves a sulfonyl radical engaged cascade process, and the selenylation is accomplished through a sequential oxidation/electrophilic cyclization process. The large-scale operation and late-stage modification experiment reveal the promising utility of this protocol.