Copper-catalyzed azide–alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(i) acetylides
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Summary
This tutorial review examines the history of the development of the CuAAC reaction, its key mechanistic aspects, and highlights the features that make it useful to practitioners in different fields of chemical science.
- Type
- review
- Published
- 2010-03-04
- Cited by
- 1,853
- References
- 68
- Access
- Open access
- OpenAlex
- https://openalex.org/W2069805392
- Semantic Scholar
- https://api.semanticscholar.org/CorpusID:32635897
Keywords
Cycloaddition, Bioconjugation, Alkyne, Combinatorial chemistry, Chemistry
References
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- "Clickphine": a novel and highly versatile P,N ligand class via click chemistry.
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- Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.
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- 1,3-Dipolar Cycloadditions. Past and Future†
- Coordination chemistry of organic azides and amination reactions catalyzed by transition metal complexes
- Enhanced Reactivity of Dinuclear Copper(I) Acetylides in Dipolar Cycloadditions
- Observation of unusual kinetics in Heck reactions of aryl halides: the role of non-steady-state catalyst concentration.
- Polymer-Supported Copper(I) Catalysts for the Experimentally Simplified Azide–Alkyne Cycloaddition
- Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles with Nitriles
- Structures of copper complexes of the hybrid [SNS] ligand of bis(2-(benzylthio)ethyl)amine and facile catalytic formation of 1-benzyl-4-phenyl-1H-1,2,3-triazole through click reaction.
- Structurally diverse dendritic libraries : A highly efficient functionalization approach using Click chemistry
- Ligand-accelerated Cu-catalyzed azide-alkyne cycloaddition: a mechanistic report.
- Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine.
- Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition.
- Acetylenic Coupling: A Powerful Tool in Molecular Construction.
- Isolation of a copper(I) triazolide: a "click" intermediate.
- Cu-catalyzed azide-alkyne cycloaddition.
- Synthesis and Reactivity of Rhodium(II) N-Triflyl Azavinyl Carbenes
Cited by
- Triazole: a unique building block for the construction of functional materials.
- Synthesis of ferrocene-labeled steroids via copper-catalyzed azide-alkyne cycloaddition. Reactivity difference between 2β-, 6β- and 16β-azido-androstanes.
- How a simple "clicked" PEGylated 1,2,3-triazole ligand stabilizes gold nanoparticles for multiple usage.
- Novel process windows for enabling, accelerating, and uplifting flow chemistry.
- L-Proline: an efficient N,O-bidentate ligand for copper-catalyzed aerobic oxidation of primary and secondary benzylic alcohols at room temperature.
- Polar red-emitting rhodamine dyes with reactive groups: synthesis, photophysical properties, and two-color STED nanoscopy applications.
- Metal Free Azide-Alkyne Click Reaction: Role of Substituents and Heavy Atom Tunneling.
- Catalyst-free synthesis of 4-acyl-NH-1,2,3-triazoles by water-mediated cycloaddition reactions of enaminones and tosyl azide
- Modification of polyhydroxyalkanoates: Evaluation of the effectiveness of novel copper(II) catalysts in click chemistry.
- Three thiacalix[4]arene-based Cu(i) coordination polymers: catalytic activities for azide-alkyne cycloaddition reactions and luminescence properties.
- Photo-Switchable Control of Membrane Properties of Liposomes and Biochemical Processes
- Renewable Bio-Based Polymers and Degradable Functional Polymers
- Mechanistic Basis for Regioselection and Regiodivergence in Nickel-Catalyzed Reductive Couplings
- In situ construction of three anion-dependent cu(i) coordination networks as promising heterogeneous catalysts for azide-alkyne "click" reactions.
- Functional Materials as Bone Adhesive for Fracture Stabilization
- Sulfonoketenimides as key intermediates for the synthesis of 2-thioxo-2HH-1,3-thiazines and 2-arylimino-2HH-1,3-thiazines
- Molecular Structure of (1-Benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)(4-bromophenyl)methanone: A Combined Experimental and Theoretical Study
- A layered double hydroxide, a synthetically useful heterogeneous catalyst for azide−alkyne cycloadditions in a continuous-flow reactor
- Synthesis, Evaluation and Applications of Biologically Significant Molecules and their Analogues
- Synthèse par cycloaddition 1,3-dipolaire d’hétérocycles et spiro-hétérocycles glycosylés comme inhibiteurs de la glycogène phosphorylase et agents anti-hyperglycémiants : évaluation et tests biologiques
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