Isoquinoline-catalyzed visible-light-mediated 1,2-/1,4-thiosulfonylation difunctionalization reaction of thiosulfates with alkenes

Abstract

We have developed a novel method for the 1,2-/1,4-thiosulfonylation bifunctional reaction of thiosulfates with non-aromatic olefins. This approach eliminates the need for metal catalysts or photocatalysts, offering an environmentally friendly, convenient, and efficient process. Under visible light irradiation, inexpensive and readily available isoquinoline serves as an energy transfer catalyst to facilitate the homolytic cleavage of the S–SO₂ bond in thiosulfates, enabling the 1,2-/1,4-thiosulfonylation bifunctionalization of either a single non-aromatic olefin or two different non-aromatic olefins, thereby constructing C–S and C–SO₂ bonds in one step. This method is expected to provide significant impetus for innovative advancements in the fields of organic synthesis methodology and medicinal chemistry.