Bismuth A3-Corroles: Useful Precursors for the Development of meso-Substituted Free-Base Corroles

Felix Faschinger; Stefan Aichhorn; Markus Himmelsbach; Wolfgang Schoefberger

doi:10.1055/s-0034-1379012

Synthesis, Table of Contents

Synthesis 2014; 46(22): 3085-3096
DOI: 10.1055/s-0034-1379012

paper

Bismuth A₃-Corroles: Useful Precursors for the Development of meso-Substituted Free-Base Corroles

Authors

Felix Faschinger

^aInstitute of Organic Chemistry, Johannes Kepler University Linz (JKU), Altenberger Straße 69, 4040 Linz, Austria Email: wolfgang.schoefberger@jku.at
Stefan Aichhorn

^aInstitute of Organic Chemistry, Johannes Kepler University Linz (JKU), Altenberger Straße 69, 4040 Linz, Austria Email: wolfgang.schoefberger@jku.at
Markus Himmelsbach

^cInstitute of Analytical Chemistry, Johannes Kepler University Linz (JKU), Altenberger Straße 69, 4040 Linz, Austria
Wolfgang Schoefberger*

^aInstitute of Organic Chemistry, Johannes Kepler University Linz (JKU), Altenberger Straße 69, 4040 Linz, Austria Email: wolfgang.schoefberger@jku.at

^bFaculty of Science, University of South Bohemia, Branišovská 31, 37005 České Budějovice, Czech Republic

Abstract

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Dedicated to Prof. Dr. Heinz Falk on the occasion of his 75^th birthday

Abstract

Systematic studies on regioselective functionalization reactions employing oxygen-, nitrogen-, and sulfur-containing nucleophiles with bismuth A₃-corroles under the influence of a strong non-nucleophilic base are reported. In the case of the thiols and dithiols a high-yielding reaction procedure was established to obtain mono-, di-, and tri-functionalized corroles at room temperature within short reaction times. The described method offers a possibility to attach bifunctional linker molecules to the para-position of the meso-pentafluorophenyl groups at positions 5, 10, and 15 of the corrole macrocycle. The described reaction strategy may serve as a versatile protocol for the covalent binding of corroles to proteins or antibodies and may be utilized to attach corroles on, for example, gold or titanium surfaces to study surface-supported reactions.

Key words

corrole - bismuth - nucleophiles - regioselective - S_NAr reaction

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References

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