Issue 21, 2013

Efficient pseudo-five-component coupling-Fiesselmann synthesis of luminescent oligothiophenes and their modification

Abstract

(Hetero)aryl bis-acid chlorides and terminal alkynes, or likewise acid chlorides and terminal dialkynes, and ethyl 2-mercaptoacetate can be reacted to give highly luminescent symmetrical terthiophenes and quinquethiophenes in the sense of a consecutive pseudo-five-component reaction in good to excellent yields. Further functionalization of the obtained oligomers can be readily achieved by halogenation followed by a metal-catalyzed coupling reaction to give α,ω-diester substrates for subsequent transformations into highly functionalized materials.

Graphical abstract: Efficient pseudo-five-component coupling-Fiesselmann synthesis of luminescent oligothiophenes and their modification

Supplementary files

Article information

Article type
Paper
Submitted
21 Jan 2013
Accepted
19 Mar 2013
First published
20 Mar 2013

Org. Biomol. Chem., 2013,11, 3541-3552

Efficient pseudo-five-component coupling-Fiesselmann synthesis of luminescent oligothiophenes and their modification

M. Teiber, S. Giebeler, T. Lessing and T. J. J. Müller, Org. Biomol. Chem., 2013, 11, 3541 DOI: 10.1039/C3OB40124C

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