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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.
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
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.

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Related Experiment Video

Updated: Jun 19, 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

Apparent copper(II)-accelerated azide-alkyne cycloaddition.

Wendy S Brotherton1, Heather A Michaels, J Tyler Simmons

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

Organic Letters
|October 9, 2009
PubMed
Summary
This summary is machine-generated.

Copper(II) salts catalyze azide-alkyne cycloadditions in alcohol without reductants. This process involves Cu(II) reduction to active Cu(I) species, enabling rapid reactions like the one between 2-picolylazide and propargyl alcohol.

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

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Last Updated: Jun 19, 2026

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Click Chemistry

Background:

  • Azide-alkyne cycloaddition reactions are fundamental in synthetic chemistry.
  • Copper-catalyzed azide-alkyne cycloaddition (CuAAC) typically requires a Cu(I) source or a reductant to generate it in situ.
  • Developing efficient CuAAC protocols that avoid external reductants is desirable for streamlined synthesis.

Purpose of the Study:

  • To investigate the catalytic activity of Copper(II) salts in azide-alkyne cycloaddition reactions in alcoholic solvents.
  • To elucidate the mechanism of Cu(II) reduction to active catalytic species.
  • To demonstrate the efficiency of this method using a specific substrate combination.

Main Methods:

  • Spectroscopic analysis (UV-Vis, EPR) to monitor copper species.
  • Reaction kinetics studies to determine reaction rates and catalyst loading.
  • Use of various Cu(II) salts and substrates in alcoholic solvents.

Main Results:

  • Cu(II) salts effectively catalyze azide-alkyne cycloadditions in alcoholic solvents without added reductants.
  • Spectroscopic data indicate in situ reduction of Cu(II) to catalytic Cu(I) species via alcohol oxidation and/or alkyne homocoupling during an induction period.
  • Chelation of 2-picolylazide to Cu(II) may facilitate the reaction.
  • The reaction between 2-picolylazide and propargyl alcohol is highly exothermic and rapid (1-2 min) with 1 mol% Cu(OAc)(2).

Conclusions:

  • Cu(II) salts can serve as efficient precatalysts for azide-alkyne cycloadditions in alcoholic media.
  • The reaction proceeds through an in situ generated Cu(I) catalytic species.
  • This method offers a simplified and accelerated approach to click chemistry, particularly for substrates like 2-picolylazide.