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

• DOI: 10.1021/acs.orglett.4c04533
• Publication Date: 2025-01-17T11:42:17Z
• Authors: Tian-Shu Zhang; Jia-Ming He; Yu-Tao Liu; Jing Li; Wenchang Zhuang; Hua Sun; Wen-Juan Hao; Qiong Wu; Shuai Liu; Bo Jiang
• Keywords: Diselenide; Bond cleavage; Cleavage (geology)

The translocation of an aryl group from selenium into carbon enabled by the cleavage C-Se bond is reported 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 construction two bonds C-C through sequential radical bicyclization 1,2-aryl migration under metal-free conditions. Control experiments mechanistic studies suggest that this reaction proceeds inert C(Ph)-Se bond, facilitating process. transformation one-step conversion simple diverse selenopheno[3,4-c]quinolines via radical-promoted process, holding significant potential for new seleniferous heterocycles.