Pseudo Five-Component Synthesis of 3-(Hetero)arylmethyl-2,5-di(hetero)-aryl-Substituted Thiophenes via Sonogashira–Glaser Cyclization Sequence

Fabian Klukas; Jörg Perkampus; Dominik Urselmann; Thomas J. J. Müller

doi:10.1055/s-0034-1379074

Synthesis, Table of Contents

Synthesis 2014; 46(24): 3415-3422
DOI: 10.1055/s-0034-1379074

paper

Pseudo Five-Component Synthesis of 3-(Hetero)arylmethyl-2,5-di(hetero)-aryl-Substituted Thiophenes via Sonogashira–Glaser Cyclization Sequence

Fabian Klukas

Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf, Germany Fax: +49(211)8114324 Email: ThomasJJ.Mueller@uni-duesseldorf.de

,

Jörg Perkampus

Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf, Germany Fax: +49(211)8114324 Email: ThomasJJ.Mueller@uni-duesseldorf.de

,

Dominik Urselmann

Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf, Germany Fax: +49(211)8114324 Email: ThomasJJ.Mueller@uni-duesseldorf.de

,

Thomas J. J. Müller*

Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf, Germany Fax: +49(211)8114324 Email: ThomasJJ.Mueller@uni-duesseldorf.de

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Abstract

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Abstract

The Sonogashira–Glaser sequence combined with a microwave-assisted cyclization is a powerful tool to synthesize unsymmetrically substituted conjugated thiophenes. A variety of 3-(hetero)arylmethyl-2,5-di(hetero)aryl-substituted thiophenes could be synthesized in moderate to excellent yields using a single Pd/Cu catalyst system. The presented method is strikingly simple to perform using commercially available starting materials. The obtained trisubstituted oligothiophene derivatives are interesting molecules for materials science.

Key words

copper - cross-coupling - heterocycles - multicomponent reactions - palladium - thiols

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References

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