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Synlett 2001; 2001(3): 0442-0444
DOI: 10.1055/s-2001-11409
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Triarylcorroles by Oxidative Coupling of Triaryltetrapyrranes

Raymond P. Briñas* , Christian Brückner
  • *Department of Chemistry, University of Connecticut, Storrs, CT 06269, USA; Fax + 1(8 60)4 86-29 81; E-mail: bruckner@nucleus.chem.uconn.edu
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Publication Date:
31 December 2001 (online)

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A general two-step, one-pot-synthesis of meso-triphenylcorrole from 5-phenyldipyrrane is presented. A number of p-phenyl-substituted 5-phenyldipyrranes were condensed with substituted benzaldehydes under acid catalyzed conditions to produce a mixture highly enriched in the corresponding tetrapyrranes. The crude mixtures were oxidized with DDQ or chloranil to produce the corresponding meso-triarylcorroles in good to excellent yield. The method is applicable to the synthesis of meso-triarylcorroles containing two differently substituted phenyl groups in the 5-, 15- and 10-positions, respectively.

corrole synthesis - tetrapyrrane - oxidative coupling - “2+2” condensation