Visible-Light-Mediated Copper-Catalyzed S-Arylation of Sulfenamides with Aryl Thianthrenium Salts

Abstract

The site-selective incorporation of sulfilimine functionalities into aromatic compounds provides a vital strategy for drug discovery in medicinal chemistry. However, green and sustainable methods for realizing the goal are still limited. Here, we report a copper-catalyzed S-arylation of sulfenamides with aryl thianthrenium salts irradiated by visible light without the photocatalyst, which exhibited fine functional-group compatibility and gave the desired products in high yields. Mechanistic investigations revealed that the key to achieving these results is the generation of an electron donor-acceptor (EDA) complex between sulfenamides and aryl thianthrenium salts under basic conditions.

Topics & Concepts