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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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Iron-Catalyzed SO2-Retaining Smiles Rearrangement through Decarboxylation.

Liang Zhang1, Yahao Huang1, Peng Hu1

  • 1Institute of Green Chemistry and Molecular Engineering, GBRCE for Functional Molecular Engineering, Lehn Institute of Functional Materials, School of Chemistry, Sun Yat-sen University, Guangzhou 510006, PR China.

Organic Letters
|December 6, 2024
PubMed
Summary
This summary is machine-generated.

This study introduces a novel iron-catalyzed Smiles rearrangement that retains sulfur dioxide (SO2), enabling the synthesis of valuable alkyl sulfone derivatives. This cost-effective method offers a versatile new route to challenging sulfone-containing compounds.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Catalysis

Background:

  • Radical Smiles rearrangements are key for C-C bond formation via radical addition/fragmentation.
  • Traditional Smiles rearrangements release sulfur dioxide (SO2) as a byproduct.
  • SO2-retaining Smiles rearrangements for alkyl sulfone synthesis are underexplored.

Purpose of the Study:

  • To develop a novel SO2-retaining Smiles rearrangement.
  • To utilize iron catalysis for milder reaction conditions.
  • To synthesize valuable γ- and δ-aryl substituted alkyl sulfones.

Main Methods:

  • Iron-catalyzed Smiles rearrangement initiated by decarboxylation of aliphatic carboxylic acids.
  • Exploration of substrate scope and functional group tolerance.
  • Optimization of reaction conditions for efficiency and yield.

Main Results:

  • An unprecedented iron-catalyzed SO2-retaining Smiles rearrangement was achieved.
  • The method demonstrates broad substrate scope and functional group tolerance.
  • Successful synthesis of γ- and δ-aryl substituted alkyl sulfones was accomplished.

Conclusions:

  • This study presents a mild, cost-effective, and versatile pathway to sulfone-containing compounds.
  • The developed methodology provides a promising strategy for synthesizing traditionally challenging alkyl sulfones.
  • This work expands the utility of Smiles rearrangements in organic synthesis.