Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Cycloaddition Reactions: Overview

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 Reaction

[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 Annulation

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 Activation

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.

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Correction to "Strain Release Cycloadditions of 2H-Azirines: Access to Polycyclic Heterocycles".

Organic letters·2026

Same author

Strain Release Cycloadditions of 2H-Azirines: Access to Polycyclic Heterocycles.

Organic letters·2025

Same author

TPDYs: strained macrocyclic diynes for bioconjugation processes.

Chemical communications (Cambridge, England)·2024

Same author

Tuning Co-Operative Energy Transfer in Copper(I) Complexes Using Two-Photon Absorbing Diimine-Based Ligand Sensitizers.

Angewandte Chemie (International ed. in English)·2024

Same author

Photocatalytic Thiol-Yne Reactions of Alkynyl Sulfides.

The Journal of organic chemistry·2023

Same author

Heteroleptic Copper(I)-Based Complexes Incorporating BINAP and π-Extended Diimines: Synthesis, Catalysis and Biological Applications.

Molecules (Basel, Switzerland)·2022

Same journal

Generation of Carbon and Phosphine Stereocenters via Cobaltaphotoredox-Catalyzed Enantioselective C-H Annulation.

Organic letters·2026

Same journal

Construction of β-Hydroxysulfones via a Photoinduced Four-Component Reaction.

Organic letters·2026

Same journal

The Development of a Highly Stereoselective Zn-Catalyzed (3 + 2) Cycloaddition of Azomethine Ylides and Nitroalkenes.

Organic letters·2026

Same journal

Visible-Light-Induced Nickel-Catalyzed Enantioconvergent C(sp<sup>3</sup>)-C(sp<sup>3</sup>) Coupling of α-Bromoamides with Alkene-Derived Alkylzirconocenes.

Organic letters·2026

Same journal

Pd-Catalyzed Regioselective Activation of <i>gem</i>-Difluorinated Spiro[2.2]pentanes: An Approach to 2-Fluorinated 1,3-Dienes.

Organic letters·2026

Same journal

General Cascade Esterification-Pentafluorosulfanyloxylation of Carboxylic Acids with Cyclic Ethers using Silver Pentafluorooxosulfate.

Organic letters·2026

See all related articles

Search research articles

Related Experiment Video

Updated: Apr 26, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Cu(I)-catalyzed macrocyclic Sonogashira-type cross-coupling.

Jeffrey Santandrea¹, Anne-Catherine Bédard, Shawn K Collins

¹Department of Chemistry and Centre for Green Chemistry and Catalysis, Université de Montréal , CP 6128 Station Downtown, Montréal, Québec, Canada , H3C 3J7.

Organic Letters

|July 24, 2014

Summary

This summary is machine-generated.

A novel copper-catalyzed Sonogashira-type reaction enables efficient macrocyclization. This method simplifies the synthesis of diverse macrocycles, including biologically active compounds like (S)-zearalane.

More Related Videos

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Related Experiment Videos

Last Updated: Apr 26, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Macrocyclic compounds are important in medicinal chemistry.
Traditional macrocyclization methods can be challenging, requiring dilute conditions or slow addition.

Purpose of the Study:

To develop a new, efficient method for macrocyclization.
To demonstrate the utility of this method for synthesizing biologically relevant molecules.

Main Methods:

A copper(I) chloride (CuCl) and 1,10-phenanthroline (phen) catalyst system with cesium carbonate (Cs2CO3) was used.
Sonogashira-type cross-coupling was employed for macrocyclization.
Reactions were performed at high concentrations without slow addition.

Main Results:

The developed catalytic system efficiently formed macrocycles of various sizes and functionalities.
Macrocyclizations were successful at high concentrations, simplifying experimental procedures.
The method was applied to the synthesis of (S)-zearalane, a biologically active macrocycle.

Conclusions:

A robust and operationally simple macrocyclization protocol was established.
This method offers a practical approach to synthesizing complex macrocycles.
The synthesis of (S)-zearalane highlights the potential of this methodology in drug discovery and development.