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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.6K
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.
2.6K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.2K
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
2.2K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.4K
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.
3.4K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.2K
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.
4.2K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

3.0K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
3.0K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

12.1K
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.
12.1K

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Visible-light-driven cascade cyclization: a modular approach to functionalized 4-pyrrolin-2-ones.

Rupashri Dash1, Karan Ramdas Thombare1, Anindya Das1

  • 1Department of Chemistry, Indian Institute of Technology Jodhpur, Karwar-342037, Rajasthan, India. sandipmurarka@iitj.ac.in.

Chemical Communications (Cambridge, England)
|September 29, 2025
PubMed
Summary
This summary is machine-generated.

A new visible-light-driven ruthenium(II) photocatalysis strategy efficiently synthesizes functionalized 4-pyrrolin-2-ones. This radical cascade cyclization method offers a versatile route to diverse scaffolds using readily available precursors.

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Synthetic Methodology

Background:

  • 4-pyrrolin-2-ones are important heterocyclic scaffolds.
  • Efficient synthesis of functionalized 4-pyrrolin-2-ones is crucial for drug discovery and materials science.
  • Existing synthetic methods may lack efficiency, scope, or functional group tolerance.

Purpose of the Study:

  • To develop an efficient and modular strategy for synthesizing densely functionalized 4-pyrrolin-2-ones.
  • To explore a visible-light-driven Ru(II) photocatalysis approach.
  • To enable diversity-oriented synthesis of valuable heterocyclic compounds.

Main Methods:

  • Visible-light-driven Ru(II) photocatalysis.
  • Radical cascade cyclization using diaryliodonium salts (DAIRs) and N-(acyloxy)phthalimides (NHPI esters) as radical precursors.
  • Expansion of the methodology to include trifluoromethyl and arylsulfonyl radicals.

Main Results:

  • Efficient construction of benzylated and alkylated 4-pyrrolin-2-one scaffolds.
  • Successful incorporation of trifluoromethyl and arylsulfonyl groups.
  • Demonstration of a broad substrate scope and high functional group tolerance.
  • Scalability of the developed protocol.

Conclusions:

  • The reported strategy provides a robust and versatile method for synthesizing diverse 4-pyrrolin-2-ones.
  • Visible-light photocatalysis offers an attractive alternative for constructing complex heterocyclic structures.
  • The methodology holds significant synthetic utility for accessing valuable chemical entities.