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

An efficient and novel approach to accessing 3-selenylquinolines from diary' 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.

Automated summary

This study describes an efficient and novel approach to synthesizing 3-selenylquinolines. By utilizing a combination of CuCl2 and air as catalyst, key Se-C and C-C bonds were formed in a single step. The method showcased moderate to excellent yields under mild conditions, highlighting its versatility and usefulness.