Photoinduced Vinylogous Dearomatization

The first vinylogous dearomatization is reported. Under a photoinduced platform, various benzothiophenes functionalized by ketones at the 3-position could react with 3-methylenechroman-4-ones efficiently, leading to a variety of valuable products that contain the pharmaceutically significant chromones and 2,3dihydrobenzo[b]thiophenes concurrently. The transformations were revealed to experience hydrogen-atom transfer, dearomatization, olefin migration, and radical cross coupling.

Automated summary

The first vinylogous dearomatization reaction is reported, which utilizes a photoinduced platform. Various benzothiophenes functionalized by ketones at the 3-position could efficiently react with 3-methylenechroman-4-ones, leading to the formation of valuable products that contain pharmaceutically significant chromones and 2,3-dihydrobenzo[b]thiophenes simultaneously. The reaction involves hydrogen-atom transfer, dearomatization, olefin migration, and radical cross coupling.