A survey of acid catalysts for use in two-step, one-flask syntheses of meso-substituted porphyrinic macrocycles

Org Lett. 2000 Jun 15;2(12):1745-8. doi: 10.1021/ol005917h.

Abstract

[reaction: see text] Diverse Lewis acids and Bronsted acids were examined in the two-step, one-flask synthesis of meso-tetraphenylporphyrin, N-confused tetraphenylporphyrin, and tetraphenylsapphyrin. The scope of acid catalysis was found to be very broad, with 35 of 45 acids providing TPP in yields ranging from 5% to 58%. NC-TPP was also widely observed in yields of 1-40%, and TPS was infrequently observed in yields of <1%. Additionally, conditions were found for direct preparation of magnesium TPP and copper TPP.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acids, Noncarboxylic / chemistry*
  • Aldehydes / chemistry
  • Catalysis
  • Porphyrins / chemical synthesis*
  • Pyrroles / chemistry

Substances

  • Acids, Noncarboxylic
  • Aldehydes
  • Porphyrins
  • Pyrroles
  • tetraphenylporphyrin