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Paper | Regular issue | Vol 65, No. 10, 2005, pp.2441-2450
Published online, 12th August, 2005
DOI: 10.3987/COM-05-10506
One-pot Synthesis of A2BC-Type Free Base Porphyrins

Yasser M. Shaker and Mathias O. Senge*

*Department of Chemistry, Trinity College Dublin, Dublin 2, Ireland

Abstract

Treatment of 5,15-diarylporphyrins with a combination of organolithium and alkyl iodide reagents followed by hydrolysis with water and oxidation with DDQ gives convenient access to A2BC-type meso-tetrasubstituted free base porphyrins in a one-pot synthesis. Key intermediates are mesomeric phlorin- and porphodimethene-type anions, the latter one being able to react with electrophiles under thermodynamic control.