Triorganoindium reagents in selective palladium-catalyzed cross-coupling with iodoimidazoles: synthesis of neurodazine

J Org Chem. 2014 Oct 17;79(20):9586-93. doi: 10.1021/jo501664p. Epub 2014 Oct 1.

Abstract

Triorganoindium reagents (R3In, R = aryl, heteroaryl, alkynyl) react selectively under palladium catalysis with N-benzyl-2,4,5-triiodoimidazole to afford the C-2 monocoupling products. The reaction proceeds efficiently for a variety of aryl- and heteroarylindium reagents with the transfer of all three organic groups attached to the metal. The coupling products can be used in a subsequent two-fold cross-coupling to give trisubstituted imidazoles in good yields. This approach was employed to synthesize neurodazine and analogues in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzyl Compounds / chemistry*
  • Catalysis
  • Coordination Complexes / chemistry*
  • Imidazoles / chemistry*
  • Indicators and Reagents / chemistry*
  • Indium / chemistry*
  • Molecular Structure
  • Palladium / chemistry

Substances

  • 1-benzyl-2-(5-(3-chlorophenyl)furan-2-yl)-4,5-bis(4-methoxyphenyl)-1H-imidazole
  • Benzyl Compounds
  • Coordination Complexes
  • Imidazoles
  • Indicators and Reagents
  • N-benzyl-2,4,5-triiodoimidazole
  • Indium
  • Palladium