Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.7K
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.
2.7K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.3K
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).
2.3K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.7K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.7K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.2K
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.
2.2K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.4K
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.
10.4K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.9K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.9K

You might also read

Related Articles

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

Sort by
Same author

Iodoacetamine-Alkyne Derivatization-Based Liquid Chromatography-Mass Spectrometry Method for Quantification of Thiol Metabolites in Serum Samples of Hepatocellular Carcinoma Patients.

Metabolites·2026
Same author

Copper-Catalyzed Cascade Cross-Coupling/Cyclization of Silyl Enol Ethers for Synthesis of Polysubstituted Furans.

Organic letters·2026
Same author

Synthesis, Reactions, and Agrochemical Studies of New 4,6-Diaryl-2-hydrazinylnicotinonitriles.

International journal of molecular sciences·2025
Same author

Correction to "Tunable Synthesis of Polysubstituted Pyrroles via Silver-Catalyzed (3 + 2) Cycloaddition of α,β-Unsaturated Nitrones with Isocyanides".

The Journal of organic chemistry·2025
Same author

Tunable Synthesis of Polysubstituted Pyrroles via Silver-Catalyzed (3 + 2) Cycloaddition of α,β-Unsaturated Nitroketones with Isocyanides.

The Journal of organic chemistry·2025
Same author

Kinetic Resolution of Heterocyclic Lactams by a Photocatalytic Cobalt-Catalyzed Dehydrogenation.

Journal of the American Chemical Society·2025

Related Experiment Video

Updated: Aug 12, 2025

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.9K

Highly congested spiro-compounds via photoredox-mediated dearomative annulation cascade.

Chao Zhou1, Andrey Shatskiy1, Azamat Z Temerdashev2

  • 1Department of Chemistry, Division of Organic Chemistry, KTH Royal Institute of Technology, Teknikringen 30, 10044, Stockholm, Sweden.

Communications Chemistry
|January 25, 2023
PubMed
Summary

This study introduces a novel photoredox-mediated annulation cascade for synthesizing spirocyclic compounds. The method efficiently achieves 6-exo-trig spirocyclization, expanding access to complex molecular architectures.

More Related Videos

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.3K
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

9.4K

Related Experiment Videos

Last Updated: Aug 12, 2025

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.9K
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.3K
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

9.4K

Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Synthetic Methodology

Background:

  • Photo-mediated radical dearomatization is key for spirocyclic compound synthesis.
  • 5-exo-trig cyclizations are well-established, but 6-exo-trig cyclizations are less explored.
  • Accessing diverse spirocyclic frameworks remains a synthetic challenge.

Purpose of the Study:

  • To develop a novel dearomative annulation cascade.
  • To achieve 6-exo-trig spirocyclization via photoredox catalysis.
  • To synthesize novel spirocyclic frameworks from aromatic carboxylic acids.

Main Methods:

  • Photoredox catalysis for C-O bond activation of aromatic carboxylic acids.
  • Generation of acyl radicals via triphenylphosphine oxidation and C-O bond cleavage.
  • Intramolecular 6-exo-trig cyclization/single-electron transfer (SET)/protonation sequence.
  • Intermolecular tandem sequences involving radical addition and 5-exo-trig cyclization.

Main Results:

  • Successful synthesis of two distinct spirocyclic frameworks.
  • Efficient intramolecular formation of spiro-chromanone products.
  • Development of intermolecular tandem reactions yielding complex spirocyclic lactams.
  • Demonstration of a versatile photoredox-mediated dearomative annulation cascade.

Conclusions:

  • The developed protocol provides a powerful new route to spirocyclic compounds.
  • The methodology enables both intramolecular and intermolecular synthesis of complex spirocycles.
  • This work significantly expands the scope of photo-mediated dearomative annulations, particularly for 6-exo-trig cyclizations.