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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.7K
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.
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.8K
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.
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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.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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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.
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.4K
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).
2.4K

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Related Experiment Video

Updated: Sep 18, 2025

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Visible Light-Promoted Construction of Cage-Like Frameworks by Sequential [2 + 2] Cycloaddition.

Zhuhai Zhang1, Yu Feng1, Jianfu Chen2

  • 1School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, China.

Organic Letters
|June 21, 2025
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Summary

Researchers developed a novel visible light-promoted cycloaddition reaction for synthesizing unique cage-like molecules. This efficient method offers a one-step pathway to complex structures with high selectivity and functional group tolerance.

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Synthetic Methodology

Background:

  • Medium-ring frameworks are prevalent in natural products and pharmaceuticals.
  • Efficient and selective synthetic routes to these structures are highly sought after.
  • Cycloaddition reactions are powerful tools for constructing cyclic systems.

Purpose of the Study:

  • To develop a novel sequential [2 + 2] cycloaddition reaction.
  • To synthesize unprecedented cage-like medium-ring frameworks.
  • To establish a mild, atom-economical, and highly selective synthetic method.

Main Methods:

  • Visible light irradiation
  • Photosensitization
  • Sequential [2 + 2] cycloaddition of unsaturated N-acylindoles
  • Mechanistic studies (experimental and computational)

Main Results:

  • Formation of unprecedented cage-like medium-ring frameworks in high yields.
  • Exclusive regio- and diastereoselectivity achieved.
  • Excellent functional group tolerance and mild reaction conditions demonstrated.
  • Reaction proceeds via an energy transfer pathway in a double [2 + 2] cycloaddition process.

Conclusions:

  • A novel and efficient visible light-promoted sequential [2 + 2] cycloaddition has been developed.
  • This methodology provides a facile, single-step access to complex cage-like molecules.
  • The reaction mechanism involves an energy transfer pathway, highlighting the role of photoredox catalysis.