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Issue 23, 2015
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Corrole and nucleophilic aromatic substitution are not incompatible: a novel route to 2,3-difunctionalized copper corrolates

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Abstract

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.

Graphical abstract: Corrole and nucleophilic aromatic substitution are not incompatible: a novel route to 2,3-difunctionalized copper corrolates

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Publication details

The article was received on 02 Apr 2015, accepted on 05 May 2015 and first published on 05 May 2015


Article type: Paper
DOI: 10.1039/C5OB00659G
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 6611-6618
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    Corrole and nucleophilic aromatic substitution are not incompatible: a novel route to 2,3-difunctionalized copper corrolates

    M. Stefanelli, F. Mandoj, S. Nardis, M. Raggio, F. R. Fronczek, G. T. McCandless, K. M. Smith and R. Paolesse, Org. Biomol. Chem., 2015, 13, 6611
    DOI: 10.1039/C5OB00659G

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