Title

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

Document Type

Article

Publication Date

6-21-2015

Abstract

© 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

First Page

6611

Last Page

6618

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