Journal
ORGANIC LETTERS
Volume 9, Issue 16, Pages 3165-3168Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol071226a
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[GRAPHICS] meso-Pyrimidinyl-substituted A(2)B-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 center dot OEt2) resulted in the formation of A(2)B-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.
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