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Exogenous nitrile substrate hydroxylation by a new dicopper-hydroperoxide complex.

Lei Li1, Amy A Narducci Sarjeant, Michael A Vance

  • 1Department of Chemistry, The Johns Hopkins University, Baltimore, MD 21218, USA.

Journal of the American Chemical Society
|November 3, 2005
PubMed
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A dicopper(I) complex reacts with oxygen to form a hydroperoxo species. This intermediate undergoes thermal transformation, yielding hydroxylated nitriles and cyanide, demonstrating oxygen atom transfer from O2.

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Area of Science:

  • Coordination chemistry
  • Organometallic chemistry
  • Bioinorganic chemistry

Background:

  • Dicopper complexes are relevant models for copper-containing enzymes.
  • Understanding the reactivity of dicopper complexes with dioxygen is crucial for catalysis.
  • Nitrile functionalization remains a challenging transformation in organic synthesis.

Purpose of the Study:

  • To investigate the reaction of a dicopper(I)/phenol-ligand complex with dioxygen.
  • To elucidate the mechanism of nitrile hydroxylation and cyanide elimination.
  • To characterize the resulting copper complexes and organic products.

Main Methods:

  • Reaction of dicopper(I) complex with O2 in RCN solvents.
  • Isolation and characterization of reaction products, including a tetranuclear cluster.
  • 18O isotopic labeling to trace oxygen atom origin.

Main Results:

  • Formation of a mu-1,1-hydroperoxo dicopper(II) species upon reaction with O2.
  • Thermal transformation leading to nitrile hydroxylation and cyanide release.
  • Isolation of a cyanide-bridged tetranuclear cluster and benzaldehyde (when R = PhCH2).
  • 18O labeling confirmed the oxygen in benzaldehyde originates from O2.

Conclusions:

  • The dicopper(I)/phenol-ligand complex activates O2 to form a hydroperoxo intermediate.
  • This intermediate can undergo thermal rearrangement to achieve nitrile hydroxylation.
  • The study provides insights into copper-mediated oxygenation reactions and cyanide release mechanisms.