Copper-mediated C-S Bond Formation and C(sp2)-H Functionalization via Cascade Cyclization

Abstract

Organosulfur compounds have a wide variety of applications in pharmaceutical compounds and synthetic materials. Carbon-sulfur bonds are often found in natural and important bioactive compounds, thus the formation of C-S bonds is of high research interest. A novel method has been discovered to generate C-S bonds in tandem with C-C bond formation. This new reaction starts with aryl diynes and a sulfinate salt under copper-mediated conditions to form a new C-S bond and two new C-C bonds, which involves the functionalization of an aromatic C-H bond and a formal [3+2] cycloaddition. This thesis will discuss the reaction optimization, reaction scope and preliminary mechanistic investigations.