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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.
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.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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.
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic rearrangements are...

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Au(III)-Catalyzed Domino Cyclization/Functionalization Reactions: an Entry to Heterocycles.

Antoine Versini1, Quentin Arias2, Nguyen Huy Hoang Vo2

  • 1Faculté de Pharmacie de Paris, UMR CNRS 8038, Université Paris Cité, CNRS, 4 Avenue de l'Observatoire, 75006 Paris, France.

The Journal of Organic Chemistry
|June 3, 2026
PubMed
Summary

This study introduces efficient gold(III)-catalyzed domino reactions for synthesizing biologically relevant polyheterocyclic compounds. The novel gold(III) catalyst demonstrates high reactivity and functional group tolerance, overcoming challenges in organic synthesis.

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Area of Science:

  • Organic chemistry
  • Catalysis
  • Medicinal chemistry

Background:

  • Synthesizing highly functionalized polyheterocyclic compounds efficiently remains a challenge.
  • Transition-metal catalysis, particularly gold complexes, offers promising synthetic routes.

Purpose of the Study:

  • To develop straightforward gold(III)-catalyzed domino reactions for accessing biologically relevant scaffolds.
  • To explore the catalytic potential of NHC-type gold(III) complexes in organic synthesis.

Main Methods:

  • Gold(III)-catalyzed domino cyclization/functionalization reactions.
  • Synthesis of isochromenes via cyclofunctionalization of 2-ethynylarylaldehyde derivatives.
  • Cycloisomerization of 1,6-enynes into (poly)heterocyclic compounds.

Main Results:

  • Achieved straightforward synthesis of complex polyheterocyclic structures.
  • Demonstrated successful application in synthesizing isochromenes and other heterocycles.
  • The NHC-type gold(III) catalyst exhibited high functional group tolerance and reactivity.

Conclusions:

  • The developed gold(III)-catalyzed methodology provides efficient access to valuable heterocyclic scaffolds.
  • NHC-type gold(III) complexes show significant potential for catalyzing diverse synthetic transformations.
  • This work advances the synthesis of biologically relevant molecules using novel catalytic approaches.