Synthesis of\n2,3-Diperfluoroalkylated Quinoxalines\nvia Selenium-Catalyzed Reductive C–C Coupling of Vicinal Perfluoroalkyl\nFormimidoyl Chlorides

A direct and efficient approach to access structurally\ninteresting\n2,3-diperfluoroalkylated quinoxalines via selenium-catalyzed reductive\nC–C construction of vicinal bis(perfluoroalkyl formimidoyl\nchloride)s has been disclosed. This protocol features the use of easily\naccessible starting materials, scalability, and a diverse functional\ngroup tolerance. Mechanism studies suggested that this reaction may\ninvolve an interesting selenium-containing seven-membered-ring intermediate\nand proceed through an electrocyclization/selenium reductive elimination\npathway, which is significantly different from the traditional transition-metal-catalyzed\nreductive coupling strategies of alkyl halides.