Document Type
Article
Publication Date
8-1-2010
Abstract
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
First Page
752
Last Page
757
Recommended Citation
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
