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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.

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Related Experiment Video

Updated: Jun 9, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Chelation-assisted, copper(II)-acetate-accelerated azide-alkyne cycloaddition.

Gui-Chao Kuang1, Heather A Michaels, J Tyler Simmons

  • 1Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA.

The Journal of Organic Chemistry
|September 3, 2010
PubMed
Summary

Chelating carbon azides significantly accelerate copper-catalyzed azide-alkyne cycloaddition (AAC) reactions. This study explores ligand effects and demonstrates the utility of resulting triazoles as metal coordination ligands.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Materials Science

Background:

  • Previous work established Cu(OAc)2 as an effective catalyst for azide-alkyne cycloaddition (AAC) without reducing agents.
  • Highly reactive carbon azides, 2-picolylazide and 2-azidomethylquinoline, were identified, suggesting chelation to Cu(II) enhances reaction rates.

Purpose of the Study:

  • To investigate the impact of auxiliary ligands on Cu(OAc)2-accelerated AAC reactions.
  • To explore the role of chelating carbon azides in enhancing catalytic efficiency.
  • To demonstrate the application of derived 1,2,3-triazoles as multidentate ligands.

Main Methods:

  • Examined the efficiency of Cu(OAc)2-accelerated AAC reactions with various carbon azides and auxiliary ligands.
  • Utilized X-ray crystallography to confirm chelation between carbon azide 11 and Cu(II).
  • Characterized metal complexes of triazolyl-containing ligands (T1, T6) using X-ray crystallography.

Main Results:

  • Carbon azides capable of chelation to the copper center exhibit superior substrate performance in Cu(OAc)2-accelerated AAC.
  • Tris(benzyltriazolylmethyl)amine (TBTA) enhances reactions with non-chelating azides, suggesting a role in Cu(II) reduction to Cu(I).
  • X-ray crystallography confirmed chelation and revealed supramolecular structures in metal complexes.

Conclusions:

  • Chelation of carbon azides to copper is crucial for efficient Cu(OAc)2-accelerated AAC reactions.
  • Chelating azides may facilitate the reduction of Cu(II) to catalytically active Cu(I) species.
  • Triazolyl-containing ligands derived from chelating azides show promise as multidentate ligands for metal coordination, sensors, and catalysts.