Corrole and nucleophilic aromatic substitution are not incompatible: A novel route to 2,3-difunctionalized copper corrolates
© The Royal Society of Chemistry 2015. The insertion of a -NO2 group onto the corrole framework represents a key step for subsequent synthetic manipulation of the macrocycle based on the chemical versatility of such a functionality. Here we report results of the investigation of a copper 3-NO2-triarylcorrolate in nucleophilic aromatic substitution reactions with "active" methylene carbanions, namely diethyl malonate and diethyl 2-chloromalonate. Although similar reactions on nitroporphyrins afford chlorin derivatives, nucleophilic attack on carbon-2 of corrole produces 2,3-difunctionalized Cu corrolates in acceptable yields (ca. 30%), evidencing once again the erratic chemistry of this contracted porphyrinoid.
Publication Source (Journal or Book title)
Organic and Biomolecular Chemistry
Stefanelli, M., Mandoj, F., Nardis, S., Raggio, M., Fronczek, F., McCandless, G., Smith, K., & Paolesse, R. (2015). Corrole and nucleophilic aromatic substitution are not incompatible: A novel route to 2,3-difunctionalized copper corrolates. Organic and Biomolecular Chemistry, 13 (23), 6611-6618. https://doi.org/10.1039/c5ob00659g