Sustainable Organocatalytic Processes to Access Alkyl SuFEx Click Hubs and Tetrasubstituted Carbon Centers: Potential Libraries for Multidisciplinary Applications

Abstract

In this account, we provide an overview of the recent achievements through our research programs focusing on sustainable organocatalysis. Our group have unveiled the effectiveness of specific organocatalysts in various environmentally benign conditions. We found that 1) N-heterocyclic carbene and 2) phosphazene superbases exhibit favorable performance in bulk aqueous reaction environments. In addition, 3) using organic superacid catalysts resulted in synergistic effects when hydrogen-bond donor catalysts were assembled under aqueous media. Moreover, we discovered that 4) a neutral organic salt precatalyst can generate a potent silylium Lewis acid catalyst in situ, specifically under solvent-free conditions. These innovative sustainable organocatalytic processes have successfully facilitated the conversion of raw starting materials into valuable compounds, including sulfur (VI) fluoride exchange (SuFEx) click hubs and tetrasubstituted carbon centers incorporating heteroatoms.