Synthetic Routes to 5,10,15-Triaryl-tetrabenzocorroles

• Published in: Journal of organic chemistry Vol. 76; no. 10; pp. 3765 - 3773
• Main Authors: Pomarico, Giuseppe, Nardis, Sara, Paolesse, Roberto, Ongayi, Owendi C, Courtney, Brandy H, Fronczek, Frank R, Vicente, Maria Graça H
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 20.05.2011; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Organic chemistry; Organometallic Compounds - chemistry; Physical Sciences; Porphyrins - chemical synthesis; Porphyrins - chemistry; Preparations and properties; Science & Technology; Spectrophotometry, Ultraviolet; BENZOPORPHYRINS; ROTHEMUND; VERSATILE SYNTHESIS; CORROLES; TETRAPHENYLPORPHYRINS; Condensation reaction; Demetallation; Nitrogen heterocycle; Organic bromine compounds; Copper complex; Metallocorrole; Aldehyde; Cobalt complex; Isoindole derivatives; Chemical coupling; Macrocycle; Tin complex; Cross reaction; Aromatic compound; Chemical synthesis
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo200026u

Two different synthetic routes for the preparation of 5,10,15-triaryl-tetrabenzocorroles have been developed. The first approach is based on the condensation of a tetrahydroisoindole with aryl-aldehydes, and the second pathway involves a cross-coupling reaction between a bromo-substituted corrole and a suitable substrate to form the four β-fused aryl rings. These routes are successful to lead to the target tetrabenzocorroles, obtained in both cases as the corresponding Cu complex and with the highest yield obtained via the one-step cross-coupling methodology. Demetalation of the Cu-tetrabenzocorrole produces the corresponding free base; this macrocycle was further exploited to obtain the Sn and Co complexes in good yields.