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This chapter deals with the design and applications of 1, 2, 3-triazole-based anion-binding molecular catalysts. Initially, unique properties of 1, 2, 3-triazole derivatives and the leading examples of their exploitation in the field of supramolecular chemistry are described. The distinct ability of chiral oligotriazoles as anion-binding catalysts is highlighted in their use for the asymmetric dearomatization reactions of quinolines, pyridines, and pyryliums, and the differences in catalytic performance between triazole-based catalysts and other chiral anion-binding catalysts are delineated. The latter part of this chapter introduces the design of chiral 1, 2, 3-triazolium ions as anion-binding phase-transfer catalysts and provides an overview of their applications to otherwise difficult-to-achieve asymmetric transformations. The development of multifunctional catalysts featuring 1, 2, 3-triazolium motifs and their synthetic utility are also described.

Hydrogen bond and metal–ligand coordinative interaction are widely exploited in asymmetric supramolecular catalysis for the construction of chiral catalytically active supramolecular architectures. Electrostatic interaction between cation and anion can also offer a unique platform for the design of supramolecular catalysts. This chapter describes our approaches toward the development of ionic supramolecular chiral ligands and molecular catalysts.