N-substituted 2-aminobiphenylpalladium methanesulfonate precatalysts and their use in C-C and C-N cross-couplings

J Org Chem. 2014 May 2;79(9):4161-6. doi: 10.1021/jo500355k. Epub 2014 Apr 18.

Abstract

A series of phosphine-ligated palladium precatalysts based on N-methyl- and N-phenyl-2-aminobiphenyl have been developed. Substitution at the nitrogen center prevents the presence of traces of aminobiphenyls that contain a free -NH2 group from contaminating cross-coupling products. These precatalysts produce N-substituted carbazoles upon activation, which cannot consume starting materials. These precatalysts were efficiently generated from 2-aminobiphenyl with minimal purification and found to be highly effective in Suzuki-Miyaura and C-N cross-coupling reactions.

Publication types

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

MeSH terms

  • Carbazoles / chemical synthesis*
  • Carbazoles / chemistry
  • Catalysis
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*

Substances

  • Carbazoles
  • Organometallic Compounds
  • Palladium