Arylselenyl Radical-Mediated Cyclization of N-(2-Alkynyl)anilines: Access to 3-Selenylquinolines

Abstract

An efficient and novel approach to accessing 3-selenylquinolines from diaryl diselenides and acyclic, selenium-free substrates is described. Preliminary mechanistic studies indicate that the combination of CuCl₂ and air affords an appropriate environment for producing arylselenyl radicals that initiate the cascade cyclization of N-(2-alkynyl)anilines, forming key Se-C and C-C bonds in a single step. Using this chemistry, a wide variety of 3-selenylquinolines were produced in moderate to excellent yield under mild conditions, highlighting the versatility and usefulness of this new method.