One-pot synthesis of meso-formylporphyrins by S(N)Ar reaction of 5,15-disubstituted porphyrins with (2-pyridyldimethylsilyl)methyllithium

Org Lett. 2008 Feb 21;10(4):685-7. doi: 10.1021/ol703107t. Epub 2008 Jan 17.

Abstract

A simple, one-pot procedure that converts 5,15-substituted porphyrins into the corresponding meso-formylated porphyrins has been developed. The method, based on a new synthetic concept for functionalized porphyrins utilizing the (2-pyridyldimethylsilyl)methyl group as a latent formyl functionality, affords the desired product in good yield and is especially appropriate for the direct formylation of free base porphyrins, which has never been achieved by known methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Lithium / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Porphyrins / chemical synthesis*
  • Porphyrins / chemistry*
  • Silicon / chemistry*
  • Stereoisomerism

Substances

  • Organometallic Compounds
  • Porphyrins
  • Lithium
  • Silicon