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. © 2011 American Chemical Society.
Pomarico, G., Nardis, S., Paolesse, R., Ongayi, O., Courtney, B., Fronczek, F., et al. (2011). Synthetic routes to 5,10,15-triaryl-tetrabenzocorroles. JOURNAL OF ORGANIC CHEMISTRY, 76(10), 3765-3773 [10.1021/jo200026u].
Synthetic routes to 5,10,15-triaryl-tetrabenzocorroles
NARDIS, SARA;PAOLESSE, ROBERTO;
2011-01-01
Abstract
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. © 2011 American Chemical Society.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
