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Related Experiment Videos

Indirect electroreductive cyclization and electrohydrocyclization using catalytic reduced nickel(II) salen.

James A Miranda1, Carolyn J Wade, R Daniel Little

  • 1Department of Chemistry & Biochemistry, University of California Santa Barbara, Santa Barbara, California 93106, USA.

The Journal of Organic Chemistry
|November 10, 2005
PubMed
Summary

Nickel(II) salen effectively mediates electroreductive cyclization (ERC) and electrohydrocyclization (EHC) reactions, achieving high yields. Mechanistic studies reveal a continuum of nickel(II) salen reduced forms, adapting to substrate electronic needs.

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Area of Science:

  • Electrochemistry
  • Organic Synthesis
  • Catalysis

Background:

  • Electrochemical reactions offer sustainable synthetic routes.
  • Nickel complexes are explored as mediators in organic transformations.
  • Understanding reaction mechanisms is crucial for optimizing catalytic processes.

Purpose of the Study:

  • To investigate the efficacy of nickel(II) salen as a mediator for electroreductive cyclization (ERC) and electrohydrocyclization (EHC).
  • To explore the mechanistic pathways of these reactions.
  • To compare the performance of nickel(II) salen with other nickel and cobalt complexes.

Main Methods:

  • Electrochemical synthesis using mercury pool or reticulated vitreous carbon (RVC) cathodes.
  • Voltammetric analysis to study mediator and substrate behavior.

Related Experiment Videos

  • Characterization of reaction products and byproducts.

    • Main Results:

    • Nickel(II) salen successfully mediated ERC and EHC reactions in 60-94% yields.
    • Structurally modified nickel(II) salen (31) acted as an electrogenerated base, forming an intramolecular Michael adduct (23).
    • A mechanistic continuum involving metal-centered and ligand-centered reduced nickel species was proposed.

    Conclusions:

    • Nickel(II) salen is an effective mediator for ERC and EHC reactions.
    • The reaction mechanism involves a flexible equilibrium between different reduced nickel species.
    • Mediator structure significantly influences the reaction pathway, enabling base-mediated cyclization.