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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.
[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.
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).
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.
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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.

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Related Experiment Video

Updated: May 17, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Azide-alkyne Huisgen [3+2] cycloaddition using CuO nanoparticles.

Hyunje Woo1, Hyuntae Kang, Aram Kim

  • 1Department of Chemistry, Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, Korea. chemistry@pusan.ac.kr

Molecules (Basel, Switzerland)
|November 8, 2012
PubMed
Summary

Copper oxide (CuO) nanoparticles are synthesized for click chemistry applications. Novel nanoreactors and hybrid nanoparticles show high catalytic activity and recyclability for azide-alkyne cycloaddition reactions.

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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

Related Experiment Videos

Last Updated: May 17, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

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

Area of Science:

  • Materials Science
  • Nanotechnology
  • Organic Chemistry

Background:

  • Click chemistry, particularly the [3+2] cycloaddition of azides with terminal alkynes, is crucial in various scientific fields.
  • Developing efficient and recyclable catalysts is essential for sustainable chemical synthesis.

Purpose of the Study:

  • To review recent advancements in CuO nanoparticle synthesis.
  • To explore the application of these nanoparticles in click chemistry reactions.
  • To introduce novel nanoreactor designs for improved catalytic processes.

Main Methods:

  • Synthesis of various CuO nanostructures, including hollow CuO NPs, CuO NPs on acetylene black, and ZnO–CuO hybrid NPs.
  • Development of water-soluble double-hydrophilic block copolymer (DHBC) nanoreactors.
  • Application of non-conventional energy sources like microwaves and ultrasound to catalyze click reactions.

Main Results:

  • The synthesized CuO-based nanomaterials demonstrated good catalytic activity and high regioselectivity in click reactions.
  • CuO hollow NPs supported on acetylene black exhibited excellent recyclability over nine cycles without activity loss.
  • Water-soluble DHBC nanoreactors facilitated an environmentally friendly click chemistry process.

Conclusions:

  • Advanced CuO nanomaterials offer efficient catalytic solutions for click chemistry.
  • Recyclable nanostructures and water-based systems pave the way for greener synthetic methodologies.
  • The reviewed developments highlight the potential of nanotechnology in advancing catalytic organic synthesis.