General synthesis of meso-amidoporphyrins via palladium-catalyzed amidation

Org Lett. 2004 May 27;6(11):1837-40. doi: 10.1021/ol049440b.

Abstract

A series of meso-amidoporphyrins were facilely synthesized by direct reactions of meso-brominated porphyrins with amides via palladium-catalyzed amidation reaction. Using a combination of palladium precursor Pd(OAc)(2) or Pd(2)(dba)(3) and phosphine ligand Xantphos, both 5-bromo-10,20-diphenylporphyrin and 5,15-dibromo-10,20-diphenylporphyrin, as well as their zinc complexes, can be effectively coupled with a wide variety of amides to give the corresponding mono- and bis-substituted meso-amidoporphyrins in high yields under mild conditions. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Bromine / chemistry
  • Catalysis
  • Ligands
  • Molecular Structure
  • Palladium / chemistry*
  • Porphyrins / chemical synthesis*
  • Porphyrins / chemistry*

Substances

  • Amides
  • Ligands
  • Porphyrins
  • Palladium
  • Bromine