Huisgen’s Cycloaddition Reactions: A Full Perspective

Abstract

Huisgen cycloaddition reaction has been originally utilized for the synthesis of 1, 2, 3-triazoles regioisomers. In this review, its stereochemistry and also mechanistical features of Huisgen cycloaddition reaction based on the quantum chemistry are highlighted.Thermal and copper catalyzed approaches to the synthesis of 1,2,3-triazoles will also be re-visited. Finally, the synthesis of alternative region-isomer, 1,5-disubstituted-1,2,3-triazoles under ruthenium catalysis and transition metal free conditions is described.

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

“…While this ruthenium-catalyzed azide alkyne cycloaddition (RuAAC) has as yet not found as prevalent use as the CuAAC reaction, reports of its application are increasing rapidly. Although, the RuAAC reaction has been briefly mentioned in several reviews on triazole formation [13][14][15][16][17][18][19][20][21][22][23] and metalcatalyzed reactions, [24][25][26] by now a comprehensive survey focused solely on RuAAC is needed.…”

Computational investigations of click-derived 1,2,3-triazoles as keystone ligands for complexation with transition metals: a review

“…In Scheme 26, the production of {Re(CO) 3 Cl} bidentate 2-pyridyl-1,2,3-triazole coordination compounds was illustrated via the reaction of the cycloadducts with the commercially available [Re(CO) 5 Cl]. X-ray diffraction analysis was also performed to identify the structural properties of the aforementioned rhenium complexes and the results compared with the DFT-optimized geometries (via C-PCM computations in methanol solution).…”

In situpreparation and characterization of novel CuI‐functionalized poly[(methyl methacrylate)‐co‐maleimide] as an efficient heterogeneous catalyst in the regioselective synthesis of 1,2,3‐triazoles via click reaction: Experimental and computational chemistry

“…The Huisegn 1,3‐dipolar azide/alkyne cycloaddition reaction represents a valuable process with wide scope and molecular diversity which was first implemented and reported by German chemist Rolf Huisgen in 1961. As a matter of fact, Huisegn 1,3‐dipolar cycloaddition is refers to an uncatalysed reaction between an azide and a terminal or internal alkyne, leading to 1,2,3‐triazoles . This reaction particularly attracted the attention of the US chemist Barry K. Sharpless (2001 Nobel Laureate) who referred to Cu(I)‐catalysed 1,3‐dipolar cycloaddition as ‘the cream of the crop’ of ‘click chemistry’ .…”

“…As a matter of fact, Huisegn 1,3-dipolar cycloaddition is refers to an uncatalysed reaction between an azide and a terminal or internal alkyne, leading to 1,2,3-triazoles. [32] This reaction particularly attracted the attention of the US chemist Barry K. Sharpless (2001 Nobel Laureate) who referred to Cu(I)-catalysed 1,3-dipolar cycloaddition as 'the cream of the crop' of 'click chemistry'. [33] The Cu(I)-catalysed 1,3-dipolar cycloaddition reaction of organic azides and terminal alkynes gives 1,4disubstituted 1,2,3-triazoles regioselectively under mild reaction conditions.…”