N-substituted imines by the copper-catalyzed N-imination of boronic acids and organostannanes with O-acyl ketoximes

Org Lett. 2007 May 10;9(10):1947-50. doi: 10.1021/ol070561w. Epub 2007 Apr 20.

Abstract

Catalytic quantities of copper(I) or copper(II) sources catalyze the N-imination of boronic acids and organostannanes through reaction with oxime O-carboxylates under nonbasic conditions. This method tolerates various functional groups and takes place efficiently using aryl, heteroaryl, and alkenyl boronic acids and stannanes.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Boronic Acids / chemical synthesis
  • Boronic Acids / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Cross-Linking Reagents / chemistry
  • Imines / chemistry*
  • Molecular Structure
  • Nitriles / chemistry
  • Oximes / chemistry*

Substances

  • Boronic Acids
  • Cross-Linking Reagents
  • Imines
  • Nitriles
  • Oximes
  • Copper