Synthesis of meso-tetraphenyl porphyrins via condensation of dipyrromethanes with N-tosyl imines

TEMELLİ B., ÜNALEROĞLU C.

TETRAHEDRON, vol.65, no.10, pp.2043-2050, 2009 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 65 Issue: 10
  • Publication Date: 2009
  • Doi Number: 10.1016/j.tet.2009.01.009
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2043-2050
  • Keywords: Porphyrin, Dipyrromethane, Metal triflate, N-Tosyl imine, ONE-FLASK SYNTHESIS, PHOTODYNAMIC THERAPY, MESOSUBSTITUTED DIPYRROMETHANES, SUBSTITUTED PORPHYRIN, AEROBIC OXIDATION, ORGANIC-SYNTHESIS, FACILE SYNTHESIS, PURE PORPHYRINS, ACID CATALYSTS, PYRROLES
  • Hacettepe University Affiliated: Yes

Abstract

A new synthetic route for the synthesis of 5,10,15,20-tetraphenyl porphyrins has been developed based on the reaction of 5-substituted dipyrromethanes with N-tosyl imines in the presence of a metal triflate catalyst. meso-Substituted tetraphenyl porphyrins were synthesized in a two-step process. The first step of the method is the metal triflate-catalyzed condensation of 5-substituted dipyrromethanes with N-tosyl imines to form a porphyrinogen intermediate and the second step is the oxidation of the porphyrinogen to porphyrin. The method was applied to the synthesis of trans-A(2)B(2)-tetraarylporphyrins and the products were obtained with only a trace amount of one scrambling product. The synthesis of two important building blocks for porphyrin synthesis, mono and di-sulfonamide alkylated 5-substituted dipyrromethanes, was achieved by the addition of 5-substituted dipyrromethane to N-tosyl imine. The application of mono and di-sulfonamide alkylated 5-substituted dipyrromethanes in '2+2' porphyrin formation reactions is presented. (C) 2009 Elsevier Ltd. All rights reserved.