Visible-light-driven radical 1,3-addition of selenosulfonates to vinyldiazo compounds

Herein, we report a visible-light-driven radical 1,3-selenosulfonylation of vinyldiazo compounds with selenosulfonates, providing various gamma-seleno allylic sulfones in good yields. This photochemical reaction was carried out at room temperature in an open flask using ethyl acetate as the solvent without any photocatalysts or additives. The control experiments corroborated that the 1,3-addition proceeded via a radical-chain propagation process. The synthetic applications of the resulting products were demonstrated by deselenization, reduction, bromination and allylation.

Automated summary

This research reports a visible-light-driven radical 1,3-selenosulfonylation of vinyldiazo compounds with selenosulfonates, yielding various gamma-seleno allylic sulfones. The reaction was carried out at room temperature in an open flask using ethyl acetate as the solvent without the need for any photocatalysts or additives. Synthetic applications of the resulting products were demonstrated through deselenization, reduction, bromination, and allylation.