Efficient microwave-assisted synthesis of amine-substituted tetrakis(pentafluorophenyl)porphyrin

Org Lett. 2006 Oct 26;8(22):4985-8. doi: 10.1021/ol060946z.

Abstract

We report an efficient and rapid means for the synthesis of tetrakis(pentafluorophenyl)porphyrin (TPPF(20)) derivatives by microwave irradiation in an environmentally acceptable solvent. The selective displacement of the para-fluorine groups in TPPF(20) by primary amines occurs in yields between 70 and 95%. This method demonstrates that TPPF(20) is an ideal platform for the rapid formation of porphyrin conjugates for therapeutic, catalytic, and other applications. [reaction: see text]

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amines / chemistry*
  • Catalysis
  • Crystallography, X-Ray
  • Microwaves*
  • Molecular Conformation
  • Molecular Structure
  • Porphyrins / chemical synthesis*
  • Porphyrins / chemistry
  • Stereoisomerism

Substances

  • Amines
  • Porphyrins