One-pot synthesis of meso-alkyl substituted isocorroles: The reaction of a triarylcorrole with Grignard reagent
The reaction of 5,10,15-tritolylcorrole with EtMgBr opens the way for novel functionalizations of the corrole ring. DDQ oxidation of the macrocycle, followed by addition of the Grignard reagent, led to the formation of 5- and 10-alkyl substituted isocorroles in satisfying yields. Together with the one-pot formation of these isocorrole isomers, the use of such a nucleophile evidenced the competitive reactivity of the macrocycle β-positions, leading to the formation of 2-bromo- and 3-bromo-5,10,15-tritolylcorrole. While the formation of these monobromocorrole derivatives is not unprecedented, this is the first time the isomers have been separated and fully characterized. Furthermore, the higher yields of the 2-substituted species highlight a useful regioselectivity for the substitution reaction. © 2010 World Scientific Publishing Company.
Publication Source (Journal or Book title)
Journal of Porphyrins and Phthalocyanines
Nardis, S., Pomarico, G., Mandoj, F., Fronczek, F., Smith, K., & Paolesse, R. (2010). One-pot synthesis of meso-alkyl substituted isocorroles: The reaction of a triarylcorrole with Grignard reagent. Journal of Porphyrins and Phthalocyanines, 14 (8), 752-757. https://doi.org/10.1142/S1088424610002513