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Iminophosphorane mediated imine metathesis.

Matthew C Burland1, Tara Y Meyer

  • 1Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.

Inorganic Chemistry
|May 28, 2003
PubMed
Summary

Iminophosphorane catalysts facilitate imine cross-metathesis reactions. A [2+2] addition/elimination mechanism is proposed, with Lewis-acid catalysis dominant for N-aryl imines.

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Area of Science:

  • Organophosphorus chemistry
  • Catalysis
  • Organic synthesis

Background:

  • Iminophosphoranes are versatile reagents in organic synthesis.
  • Catalytic cross-metathesis of imines is an important transformation.
  • Understanding reaction mechanisms is crucial for catalyst development.

Purpose of the Study:

  • To investigate the catalytic activity of iminophosphoranes in imine cross-metathesis.
  • To elucidate the reaction mechanism for imine/imine and imine/carbodiimide cross-metathesis.
  • To compare the catalytic behavior with N-alkyl and N-aryl imine substrates.

Main Methods:

  • Metathesis reactions using iminophosphorane Cl(3)P[double bond]NAr (1a).
  • Reactions conducted at 80 degrees C with various imine substrates.
  • Spectroscopic analysis to identify intermediates and products.

Main Results:

  • Compound 1a effectively catalyzed imine/imine and imine/carbodiimide cross-metathesis.
  • [double bond]NR exchange products were observed.
  • Evidence for diazaphosphetidine intermediates suggests a [2+2] addition/elimination pathway for N-alkyl imines.
  • Lewis-acid catalysis was dominant for N-aryl imines.
  • A decomposition pathway involving HCl elimination was observed for N-alkyl imines.

Conclusions:

  • Iminophosphoranes are effective catalysts for imine cross-metathesis.
  • The reaction mechanism varies depending on the imine substituent (N-alkyl vs. N-aryl).
  • The resting state of the catalyst is the iminophosphorane, not the diazaphosphetidine.

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