Visible-Light-Promoted Selective Sulfonylation and Selenylation of Dienes to Access Sulfonyl-/Seleno-benzazepine Derivatives
Zhen Zhang, Pengpeng Tan, Shilong Wang, Huichao Wang, Lei Xie, Yue Chen, Liangliang Han, Shubin Yang, Kai Sun
Abstract
A novel visible-light-promoted selective sulfonylation and selenylation of dienes with selenosulfonates has been developed. This technology provides 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.
Topics & Concepts
ChemistrySulfonylElectrophileCascadeCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisAlkylChromatographySulfur-Based Synthesis TechniquesOrganoselenium and organotellurium chemistryRadical Photochemical Reactions