meso-Pyrimidinyl-Substituted A2B-Corroles

meso-Pyrimidinyl-substituted A2B-corroles were synthesized in good yields by condensation of 5-mesityldipyrromethane and 2-substituted 4,6-dichloropyrimidine-5-carbaldehydes. A simple reduction of the amount of Lewis acid (BF3·OEt2) resulted in the formation of A2B-corroles, which was optimized to m...

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Veröffentlicht in:Organic letters 2007-08, Vol.9 (16), p.3165-3168
Hauptverfasser: Maes, Wouter, Ngo, Thien H, Vanderhaeghen, Jeroen, Dehaen, Wim
Format: Artikel
Sprache:eng
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Zusammenfassung:meso-Pyrimidinyl-substituted A2B-corroles were synthesized in good yields by condensation of 5-mesityldipyrromethane and 2-substituted 4,6-dichloropyrimidine-5-carbaldehydes. A simple reduction of the amount of Lewis acid (BF3·OEt2) resulted in the formation of A2B-corroles, which was optimized to maximize the corrole yield. Nucleophilic aromatic substitution, Suzuki, and Stille cross-coupling reactions were performed on the Cu-metalated pyrimidinylcorroles to obtain sterically encumbered triarylcorroles, while the substitution pattern at the 2-position of the pyrimidinyl substituent was altered through Liebeskind−Srogl cross-couplings.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol071226a