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Radical Smiles Rearrangements: Aryl Migration for Molecular Editing.

Xu Ha1, Xing-Ye Wang1, Saira Qurban1

  • 1State Key Laboratory of Natural Product Chemistry, College of Chemistry and Chemical Engineering, MOE Frontiers Science Center for Rare Isotopes, Lanzhou Magnetic Resonance Center, Lanzhou University, Lanzhou, Gansu, China.

Chemistry, an Asian Journal
|April 6, 2026
PubMed
Summary
This summary is machine-generated.

Visible-light photocatalysis revolutionizes Smiles and Truce-Smiles rearrangements, enabling mild radical aryl migration and molecular editing. This review details advancements in sulfonyl and sulfinyl group transformations for diverse synthetic applications.

Keywords:
aryl migrationasymmetric sulfinyl‐Smiles chemistrynucleophilic aromatic substitutionphotoredox catalysisradical Smile rearrangement

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Synthetic Methodology

Background:

  • Smiles and Truce-Smiles rearrangements traditionally involved nucleophilic aromatic substitutions.
  • Recent advancements have expanded their scope to radical aryl migration and molecular editing.

Purpose of the Study:

  • To survey the evolution of Smiles and Truce-Smiles rearrangements.
  • To highlight the impact of visible-light photoredox catalysis and related photoinduced activation modes.
  • To discuss mechanistic features and diverse applications.

Main Methods:

  • Visible-light photoredox catalysis
  • Electron-donor-acceptor (EDA) complexes
  • Energy-transfer and ligand-to-metal charge-transfer (LMCT) processes
  • Metal-hydride hydrogen atom transfer (MHAT)
  • Radical-cation pathways

Main Results:

  • Sulfonyl and sulfinyl groups are transformed into versatile aryl-migration handles.
  • Mild reaction conditions are achieved through photocatalytic and catalyst-free approaches.
  • Applications include alkene difunctionalizations, SO2 insertion/relay cascades, decarboxylative/decarbonylative arylations, and C(sp3)-H functionalization.

Conclusions:

  • Smiles rearrangements offer a powerful platform for molecular editing and synthesis.
  • Future opportunities lie in expanding substrate scope, stereocontrol, and late-stage functionalization.
  • Integration with electrochemical, flow, and data-driven catalysis holds promise for medicinal chemistry and materials science.