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Related Concept Videos

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: 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 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.
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.
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Microwave-assisted cycloaddition reactions.

Prasad Appukkuttan1, Vaibhav P Mehta, Erik V Van der Eycken

  • 1Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, B-3001, Leuven, Belgium.

Chemical Society Reviews
|April 27, 2010
PubMed
Summary
This summary is machine-generated.

Microwave irradiation significantly enhances cycloaddition reactions, accelerating the synthesis of heterocyclic compounds like 1,2,3-triazoles. This review highlights its impact on [3+2], [4+2], and [2+2] cycloaddition outcomes.

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Area of Science:

  • Synthetic Organic Chemistry
  • Green Chemistry

Background:

  • Cycloaddition reactions are fundamental in organic synthesis for creating cyclic structures.
  • Microwave irradiation is an energy-efficient technique with potential to accelerate chemical reactions.

Purpose of the Study:

  • To review the influence of microwave irradiation on various cycloaddition reactions.
  • To showcase its effectiveness in synthesizing heterocyclic compounds, including 1,2,3-triazoles.

Main Methods:

  • Review of literature examples involving [3+2], [4+2], and [2+2] cycloadditions.
  • Focus on studies demonstrating the application and impact of microwave irradiation.

Main Results:

  • Microwave irradiation demonstrably accelerates reaction rates in reviewed cycloadditions.
  • Improved yields and selectivity were observed in several microwave-assisted cycloaddition reactions.
  • The formation of 1,2,3-triazoles via [3+2] cycloaddition benefits significantly from microwave heating.

Conclusions:

  • Microwave irradiation is a powerful tool for optimizing cycloaddition reactions in organic synthesis.
  • Its application offers a greener and more efficient alternative to conventional heating methods.
  • This technique facilitates rapid and effective construction of diverse heterocyclic scaffolds.