meso-Pyrimidinyl-Substituted A2B- and A3-Corroles

• Published in: Journal of organic chemistry Vol. 75; no. 6; pp. 2127 - 2130
• Main Authors: Ngo, Thien H, Nastasi, Francesco, Puntoriero, Fausto, Campagna, Sebastiano, Dehaen, Wim, Maes, Wouter
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 19-03-2010
• Subjects: Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Organic chemistry; Preparations and properties; Suzuki coupling; Functionalization; Nitrogen heterocycle; Macrocyclization; Pyrimidine derivatives; Steric hindrance; Metallocorrole; Nucleophilic substitution; Chemical synthesis; Optimization; SNAr mechanism
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo902709c

A variety of meso-pyrimidinyl-substituted A2B- and A3-corroles (A = 4,6-dichloropyrimidin-5-yl) have been synthesized by careful optimization of the macrocyclization conditions. meso-Pyrimidinylcorroles offer the distinct advantage of an unprecedented broad scope of functionalization options. Highly sterically encumbered triarylcorroles were readily prepared via efficient nucleophilic aromatic substitution and Suzuki cross-coupling procedures.