The research on 1,2,3-triazoles has been lively and ever-growing since its stimulation by the advent of click chemistry The attractiveness of 1H-1,2,3-triazoles and their derivatives originates from their unique combination of facile accessibility via click chemistry and truly diverse supramolecular interactions, which enabled myriads of applications in supramolecular and coordination chemistry The nitrogen-rich triazole features a highly polarized carbon atom allowing the complexation of anions by hydrogen and halogen bonding or, in the case of the triazolium salts, via charge-assisted hydrogen and halogen bonds On the other hand, the triazole offers several N-coordination modes including coordination via anionic and cationic nitrogen donors of triazolate and triazolium ions, respectively After CH-deprotonation of the triazole and the triazolium, powerful carbanionic and mesoionic carbene donors, respectively, are available The latter coordination mode even features non-innocent ligand behavior Moreover, these supramolecular interactions can be combined, eg, in ion-pair recognition, preorganization by intramolecular hydrogen bond donation and acceptance, and in bimetallic complexes Ultimately, by clicking two building blocks into place, the triazole emerges as a most versatile functional unit allowing very successful applications, eg, in anion recognition, catalysis, and photochemistry, thus going far beyond the original purpose of click chemistry It is the intention of this review to provide a detailed analysis of the various supramolecular interactions of triazoles in comparison to established functional units, which may serve as guidelines for further applications

Beyond click chemistry - supramolecular interactions of 1,2,3-triazoles.

Recent advances in catalysis in micellar media

An organocatalytic azide–aldehyde [3+2] cycloaddition (organo-click) reaction of a variety of enolizable aldehydes is reported. The organo-click reaction is characterized by a high rate and regioselectivity, mild reaction conditions, easily available substrates with simple operation, and excellent yields with a broad spectrum of substrates. It constitutes an alternative to the previously known CuAAC, RuAAC, and IrAAC click reactions.

http://www.chtf.stuba.sk/~szolcsanyi/education/files/Chemia%20heterocyklickych%20zlucenin/Prednaska%203/Doplnkove%20studijne%20materialy/Triazoles/Regioselective%20Synthesis%20of%201,4-Disubstituted%201,2,3-Triazoles.pdf

An Organocatalytic Azide–Aldehyde [3+2] Cycloaddition: High‐Yielding Regioselective Synthesis of 1,4‐Disubstituted 1,2,3‐Triazoles

A metal-free three-component reaction to synthesize 1,4,5-trisubstituted 1,2,3-triazoles from readily available building blocks, such as aldehydes, nitroalkanes, and organic azides, is described. The process is enabled by an organocatalyzed Knoevenagel condensation of the formyl group with the nitro compound, which is followed by the 1,3-dipolar cycloaddition of the azide to the activated alkene. The reaction features an excellent substrate scope, and the products are obtained with high yield and regioselectivity. This method can be utilized for the synthesis of fused triazole heterocycles and materials with several triazole moieties.

A Metal‐Free Three‐Component Reaction for the Regioselective Synthesis of 1,4,5‐Trisubstituted 1,2,3‐Triazoles

http://www.chtf.stuba.sk/~szolcsanyi/education/files/Chemia%20heterocyklickych%20zlucenin/Prednaska%203/Doplnkove%20studijne%20materialy/Triazoles/Organocatalytic%20routes%20toward%20substituted%201,2,3-triazoles.pdf

Organocatalytic routes toward substituted 1,2,3-triazoles

Organocatalytic 1,3-dipolar cycloaddition reactions of ketones and azides with water as a solvent

Dioctyl prolinamide is an efficient catalyst for the 1,3-dipolar cycloaddition of ketones with azides leading to a variety of 1,2,3-triazoles (30 examples).

Dwun Kit Jonathan Yeung

Papers

Organocatalytic 1,3-dipolar cycloaddition reactions of ketones and azides with water as a solvent

Organocatalytic 1,3‐Dipolar Cycloaddition Reactions of Ketones and Azides with Water as a Solvent.

Organocatalytic 1,3-dipolar cycloaddition reaction of ketone and azides via water as a solvent