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.

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Keywords

Aromatic compounds, Carbon, Copper, Substitution reactions, Diethyl malonate, Macrocyclic compounds, Nucleophilic aromatic substitution, Polypyrroles

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Rights

©2015 The Royal Society of Chemistry. This article may not be further made available or distributed.

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