Simple and catalyst-free synthesis of meso-O-, -S-, and -C-substituted porphyrins

Org Lett. 2014 Mar 21;16(6):1590-3. doi: 10.1021/ol500191j. Epub 2014 Mar 5.

Abstract

A simple and efficient method for the meso-functionalization of porphyrin has been developed. Kinetic studies of meso-fluoro-, -chloro-, -bromo-, -iodo-, and -nitro-substituted porphyrins (Ni) with phenol reveal that the reaction undergoes a typical aromatic nucleophilic substitution (SNAr) process. This catalyst-free method can be performed with meso-brominated porphyrins and oxygen-, sulfur-, and carbon-based nucleophiles to achieve a wide variety of meso-substituted porphyrins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromine / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Kinetics
  • Metalloporphyrins / chemical synthesis*
  • Metalloporphyrins / chemistry
  • Molecular Structure
  • Nickel / chemistry
  • Oxygen / chemistry
  • Phenols / chemistry*
  • Sulfur / chemistry

Substances

  • Metalloporphyrins
  • Phenols
  • Sulfur
  • Nickel
  • Oxygen
  • Bromine