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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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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Visible-Light-Mediated Radical Truce-Smiles Rearrangement via Arylazo Sulfones.

Lorenzo Di Terlizzi1,2, Luca Nicchio1,2, Emeric Montinho-Inacio1

  • 1Institut de Chimie des Substances Naturelles (ICSN), CNRS UPR 2301, Université Paris-Saclay, 1 avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.

JACS Au
|October 31, 2025
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Summary
This summary is machine-generated.

This study introduces a new photocatalyst-free method for olefin difunctionalization using visible light and arylazo sulfones. The process efficiently creates valuable sulfonylated aryl compounds with high selectivity and stereocontrol.

Keywords:
DFT calculationsTruce−Smiles rearrangementarylazo sulfonesasymmetric synthesisphotocatalyst-freevisible light

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Photochemistry

Background:

  • The Truce-Smiles rearrangement (TSR) is a valuable reaction for C-C bond formation.
  • Developing photocatalyst-free methods for TSR under visible light is desirable for sustainable synthesis.

Purpose of the Study:

  • To develop a photocatalyst-free, visible-light-mediated TSR for olefin difunctionalization.
  • To achieve selective synthesis of β-sulfonyl-α-arylpropamides.
  • To establish a stereoselective variant using chiral auxiliaries.

Main Methods:

  • Visible-light irradiation of photoactivatable arylazo sulfones as sulfonyl radical precursors.
  • Reaction of olefins with arylazo sulfones.
  • Incorporation of a chiral amino acid auxiliary (α-tert-butyl-leucine) for stereoselective synthesis.
  • Density Functional Theory (DFT) calculations to elucidate reaction mechanisms and selectivity.

Main Results:

  • Efficient synthesis of β-sulfonyl-α-arylpropamides in high yields and stereoselectivity.
  • Development of a stereoselective TSR variant yielding optically enriched α-arylpropamides with excellent diastereoselectivity (up to 20:1 dr).
  • DFT calculations revealed key factors influencing reactivity and selectivity, including differences between N-alkyl and N-aryl acrylamides.

Conclusions:

  • This work presents a sustainable, practical, and catalyst-free method for constructing sulfonylated aryl compounds.
  • The developed method operates under mild conditions, offering a valuable tool for organic synthesis.
  • The stereoselective variant provides access to enantiomerically enriched products, expanding synthetic possibilities.