Arylselenyl Radical-Mediated Cyclization of <i>N</i>-(2-Alkynyl)anilines: Access to 3-Selenylquinolines
Changlei Zhu, Max Nurko, Cynthia S. Day, John C. Lukesh
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.
Topics & Concepts
ChemistryRadical cyclizationMedicinal chemistryCombinatorial chemistryOrganoselenium and organotellurium chemistrySulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods