Cross-Electrophile Coupling of Aryl (Pseudo)Halides and Vinyl (Pseudo)Halides

Abstract

The formation of C(sp²)–C(sp²) bonds is crucial in synthetic organic chemistry, especially for the development of pharmaceuticals. There are various approaches to create these bonds, with vinylation being one of the most significant methods. Such bonds are important as they are found in many drugs, highlighting the need for effective synthesis. Nonetheless, the vinylation process in Heck coupling presents several challenges, such as issues related to regio- and stereoselectivity, along with isomerization. In oxidative cross-coupling, difficulties arise from the presence of activated olefins, concerns about selectivity, and rigorous reaction conditions. These obstacles can be overcome by using a ligand-induced, visible-light-mediated palladium catalyst that enables selective cross-electrophile coupling between aryl (pseudo)halides and vinyl (pseudo)halides. This method utilizes differences in bond energy, resulting in more efficient reaction pathways and improving both yields and selectivity in the synthesis of C(sp²)–C(sp²) bonds.