An efficient PIFA-mediated synthesis of a directly linked zinc chlorin dimer via regioselective oxidative coupling

Org Lett. 2012 Jun 1;14(11):2746-9. doi: 10.1021/ol300969g. Epub 2012 May 14.

Abstract

The synthesis of a directly linked zinc chlorin dimer was first achieved by a facile and efficient oxidative coupling of zinc chlorin monomers with phenyliodine bis(trifluoroacetate) (PIFA). The reaction shows high regioselectivity at the 20-position near the hydrogenated pyrrole ring producing selective dichlorin in 74% yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fluoroacetates*
  • Iodobenzenes
  • Metalloporphyrins / chemistry*
  • Molecular Structure
  • Oxidative Coupling
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Stereoisomerism
  • Trifluoroacetic Acid / chemistry
  • Zinc / chemistry*

Substances

  • Fluoroacetates
  • Iodobenzenes
  • Metalloporphyrins
  • Pyrroles
  • phenyliodine(III) bis(trifluoroacetate)
  • zinc chlorin
  • Trifluoroacetic Acid
  • Zinc