Synthesis 2014; 46(22): 3085-3096
DOI: 10.1055/s-0034-1379012
paper
© Georg Thieme Verlag Stuttgart · New York

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

Felix Faschinger
a  Institute of Organic Chemistry, Johannes Kepler University Linz (JKU), Altenberger Straße 69, 4040 Linz, Austria   eMail: [email protected]
,
Stefan Aichhorn
a  Institute of Organic Chemistry, Johannes Kepler University Linz (JKU), Altenberger Straße 69, 4040 Linz, Austria   eMail: [email protected]
,
Markus Himmelsbach
c  Institute of Analytical Chemistry, Johannes Kepler University Linz (JKU), Altenberger Straße 69, 4040 Linz, Austria
,
Wolfgang Schoefberger*
a  Institute of Organic Chemistry, Johannes Kepler University Linz (JKU), Altenberger Straße 69, 4040 Linz, Austria   eMail: [email protected]
b  Faculty of Science, University of South Bohemia, Branišovská 31, 37005 České Budějovice, Czech Republic
› Institutsangaben
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Publikationsverlauf

Received: 01. Juli 2014

Accepted after revision: 01. August 2014

Publikationsdatum:
28. August 2014 (online)


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

Supporting Information

 
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