Radical-Triggered Bicyclization and Aryl Migration of 1,7-Diynes with Diphenyl Diselenide for the Synthesis of Selenopheno[3,4-<i>c</i>]quinolines
Tian-Shu Zhang, Jiaming He, Yutao Liu, Jing Li, Wenchang Zhuang, Huaming Sun, Wen-Juan Hao, Qiong Wu, Shuai Liu, Bo Jiang
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.