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

• Published in: Chemical record Vol. 17; no. 5; pp. 485 - 498
• Main Authors: Zurro, Mercedes, Mancheño, Olga García
• Format: Journal Article
• Language: English
• Published: United States Wiley Subscription Services, Inc 01.05.2017
• Subjects: Aldehydes; Alkylation; Anion-Binding Organocatalysis; Catalysis; Catalysts; Dearomatization; Heterocycles; Lewis Acid Catalysis; Metals; Physical properties; Reagents; Triazoles; Dearomatization; Heterocycles; Anion-Binding Organocatalysis; Lewis Acid Catalysis; Triazoles
• ISSN: 1527-8999; 1528-0691
• DOI: 10.1002/tcr.201600104

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. 1,2,3‐Triazoles: unique heterocycles that allow both the coordination to metals and the establishment of supramolecular interactions. In this account we illustrate our recent results in the use of chiral triazole structures in metal Lewis‐acid catalysis and anion‐binding organocatalysis.