Radical-Triggered Bicyclization and Aryl Migration of 1,7-Diynes with Diphenyl Diselenide for the Synthesis of Selenopheno[3,4-c]quinolines

Abstract

The translocation of an aryl group from selenium into carbon enabled by the cleavage of the C–Se bond is reported by using nitrogen atom-linked 1,7-diynes and diaryl diselenides as starting materials, leading to various selenophene derivatives in a regioselective manner. This method enables the construction of two C–Se bonds and two C–C bonds through sequential radical bicyclization and 1,2-aryl migration under metal-free conditions. Control experiments and mechanistic studies suggest that this reaction proceeds through the cleavage of the inert C(Ph)–Se bond, facilitating the aryl translocation process. This transformation enables the one-step conversion of simple diselenides into diverse selenopheno[3,4-c]quinolines via a radical-promoted process, holding significant potential for new seleniferous heterocycles.