1,2,3,-Triazole-Based Catalysts: From Metal- to Supramolecular Organic Catalysis

1,2,3-Triazoles are unique heterocycles with intriguing physical properties that allow not only the coordination to metals, but also the establishment of supramolecular interactions based on their polarized C-H bonds. In this account, an extensive work of our group on the design and application of 1,2,3-triazole catalysts is covered. Initially, a family of BINOL triazoles (Click-BINOLs) was synthesized and employed in model test reactions in asymmetric metal catalysis such as the Ti-catalyzed addition of alkylzinc reagents to aldehydes. The evolution from the Click-BINOLs to a novel class of triazole-based anion-binding organocatalysts is further discussed. Consequently, these catalysts were successfully applied in alkylation reactions, as well as asymmetric dearomatizations of diverse N-heteroarenes.