Mild copper-catalyzed N-arylation of azaheterocycles with aryl halides

M. Kuil, E.K. Bekedam, G.M. Visser, A. van den Hoogenband, J.W. Terpstra, P.C.J. Kamer, P.W.N.M. Leeuwen, G.P.F. Strijdonck

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Abstract

A highly efficient copper(I)-catalyzed N-arylation of azaheterocycles with various aryl halides is reported. The N-arylation reaction can be carried out using as low as 0.5 mol % of (Cu(I)OTf)2¿PhH and 1.0 mol % of 4,7-dichloro-1,10-phenanthroline as the ligand. Furthermore, cheap and stable copper precursors like Cu(I)I and Cu(II)(OAc)2¿H2O and the cheap and mild base K2CO3 can be used.
Original languageEnglish
Pages (from-to)2405-2409
JournalTetrahedron Letters
Volume46
Issue number14
DOIs
Publication statusPublished - 2005

Keywords

  • bond formation
  • c-n
  • arylboronic acids
  • nitrogen-heterocycles
  • goldberg reactions
  • ullmann synthesis
  • organic-synthesis
  • efficient
  • amination
  • imidazoles

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