Issue 32, 2014

3-NO2-5,10,15-triarylcorrolato-Cu as a versatile platform for synthesis of novel 3-functionalized corrole derivatives

Abstract

β-Nitrocorroles are potentially valuable platforms for the preparation of a wide range of more elaborated corrole derivatives possessing unique chemical functionalities and electronic properties. Here we report our results on the chemical manipulation of a copper 3-NO2-triarylcorrolate using different organic reactions, all involving the reduction of –NO2 to –NH2 at an early stage, followed by further transformations. By way of a β-acylated copper corrolate, a novel corrole derivative bearing an alkyl azide group on the peripheral positions was obtained and exploited in the Huisgen 1,3-dipolar cycloaddition.

Graphical abstract: 3-NO2-5,10,15-triarylcorrolato-Cu as a versatile platform for synthesis of novel 3-functionalized corrole derivatives

Supplementary files

Article information

Article type
Paper
Submitted
17 Jun 2014
Accepted
01 Jul 2014
First published
01 Jul 2014

Org. Biomol. Chem., 2014,12, 6200-6207

Author version available

3-NO2-5,10,15-triarylcorrolato-Cu as a versatile platform for synthesis of novel 3-functionalized corrole derivatives

M. Stefanelli, M. Mancini, M. Raggio, S. Nardis, F. R. Fronczek, G. T. McCandless, K. M. Smith and R. Paolesse, Org. Biomol. Chem., 2014, 12, 6200 DOI: 10.1039/C4OB01247J

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