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Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
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Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
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Radical Substitution: Allylic Bromination01:27

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Visible-Light-Catalyzed Cascade Radical Cyclization for 3-Substituted Chroman-4-ones.

Jie Xie1, Jie Hou1, Chunyan Bao2

  • 1Department of Polymer Materials, School of Materials Science and Engineering, Tongji university, 4800 Caoan Road, Shanghai 201804, P. R. China.

The Journal of Organic Chemistry
|November 17, 2025
PubMed
Summary

This study presents a new visible-light-catalyzed method for synthesizing 3-substituted chroman-4-one derivatives. The additive-free cascade reaction efficiently creates complex molecules at room temperature using photocatalysis.

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Radical Chemistry

Background:

  • Chroman-4-one derivatives are important scaffolds in medicinal chemistry.
  • Efficient synthesis of substituted chroman-4-ones remains a challenge.

Purpose of the Study:

  • To develop a novel, efficient, and sustainable method for synthesizing 3-substituted chroman-4-one derivatives.
  • To utilize visible-light photocatalysis for a cascade radical cyclization/addition reaction.

Main Methods:

  • Visible-light-catalyzed, additive-free cascade radical cyclization/addition reaction.
  • Photocatalytic reduction of ketoxime esters to generate nitrogen-centered radicals.
  • β-C-C bond cleavage to form carbon-centered radicals.
  • Intramolecular cyclization and radical addition with N-arylacrylamide.

Main Results:

  • Successful synthesis of diverse 3-substituted chroman-4-one derivatives.
  • The reaction proceeds efficiently at room temperature.
  • The process is initiated by photocatalytic reduction of ketoxime esters.
  • Nitrogen-centered radicals undergo cascade transformations to form the desired products.

Conclusions:

  • A novel and efficient visible-light-catalyzed cascade reaction for chroman-4-one synthesis has been established.
  • This method offers a sustainable and additive-free approach to valuable organic compounds.
  • The reaction pathway involves radical intermediates and efficient cyclization/addition steps.