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O-arylative Passerini reactions.

Laurent El Kaim1, Marie Gizolme, Laurence Grimaud

  • 1Laboratoire Chimie et procédés, Ecole Nationale Supérieure de Techniques Avancées, 32 Boulevard Victor, 75739 Paris Cedex 15, France. laurent.elkaim@ensta.fr

Organic Letters
|October 20, 2006
PubMed
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A new Passerini-type reaction efficiently synthesizes O-arylated compounds from phenols, isocyanides, and aldehydes. This novel method utilizes an irreversible Smiles rearrangement, a first for Passerini reactions.

Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Reaction Mechanisms

Background:

  • Passerini reactions are versatile tools for synthesizing complex organic molecules.
  • Smiles rearrangements are known intramolecular nucleophilic aromatic substitution reactions.
  • Integrating known reactions into new contexts can unlock novel synthetic pathways.

Purpose of the Study:

  • To develop a novel three-component reaction for synthesizing O-arylated compounds.
  • To investigate the feasibility of incorporating a Smiles rearrangement into a Passerini-type reaction.
  • To establish a new synthetic route utilizing isocyanides, phenol derivatives, and aldehydes.

Main Methods:

  • A three-component reaction involving isocyanides, phenol derivatives, and aldehydes was performed in methanol.

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  • The reaction mechanism was studied, focusing on the formation and rearrangement of intermediate adducts.
  • Spectroscopic methods were used to characterize the O-arylated products.

    • Main Results:

    • The reaction readily yielded O-arylated compounds under mild conditions.
    • An irreversible Smiles rearrangement of intermediate phenoxyimidate adducts was identified as the key step.
    • This represents the first documented instance of a Smiles rearrangement within a Passerini reaction framework.

    Conclusions:

    • A novel and efficient Passerini-type reaction has been established for O-arylated compound synthesis.
    • The successful integration of the Smiles rearrangement expands the mechanistic scope of Passerini reactions.
    • This methodology offers a new pathway for accessing valuable O-arylated organic molecules.