A novel method for the synthesis of dipyrromethanes by metal trillate catalysis


Temelli B. , Unaleroglu C.

TETRAHEDRON, vol.62, no.43, pp.10130-10135, 2006 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 62 Issue: 43
  • Publication Date: 2006
  • Doi Number: 10.1016/j.tet.2006.08.047
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.10130-10135
  • Keywords: dipyrromethanes, metal triflate, N-tosyl imine, pyrrole derivatives, Lewis acid catalysis, ORGANIC-SYNTHESIS, MESOSUBSTITUTED DIPYRROMETHANES, EXPANDED PORPHYRINS, PROTIC MEDIA, PYRROLE, INDOLES, ESTERS, TRIFLATE, DESIGN, IMINES

Abstract

5-Substituted dipyrromethanes were synthesized by the reaction of N-tosyl imines with excess pyrrole in the presence of metal triflates. Tripyrromethane and other oligomeric side products were not observed. High yields of 5-substituted dipyrromethanes were obtained for electron donating and withdrawing substituents by performing the reaction at two different temperatures. The new reaction procedure is simple and anhydrous conditions are not required. (c) 2006 Elsevier Ltd. All rights reserved.