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Synthesis 2011(20): 3375-3378  
DOI: 10.1055/s-0030-1260178
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Versatile Route to N,N′-Tetraaryl-Substituted 2,5-Diaminothiophenes

Christoph Heichert, Marion Wrackmeyer, Horst Hartmann*
Department Chemie, Technische Universität Dresden, George-Bähr-Str. 1, 01069 Dresden, Germany
Fax: +49(351)46339485; e-Mail: hartmann@iapp.de;
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Publication History

Received 20 June 2011
Publication Date:
18 August 2011 (online)

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Abstract

By reaction of N,N′-tetraaryl-substituted succinic di­amides with Lawesson’s reagent, a series of N,N′-tetraaryl-substituted 2,5-diaminothiophenes was prepared. The N,N′-tetrakis(4-bromophenyl)-2,5-diaminothiophene, thus available, was used as an educt for the synthesis of N,N′-tetrakis(4-diphenylaminophenyl)-2,5-diaminothiophene by reaction with four equivalents of diphenyl­amine in the presence of palladium as catalyst. Both the N,N′-tetraaryl-substituted 2,5-diaminothiophenes and the N,N′-tetrakis(4-diphenylaminophenyl)-2,5-diaminothiophene can be electrochemically oxidised in a stepwise manner via the corresponding radical cations into relatively stable dications. The latter compounds can also be oxidised into tetracationic species.

Key words

amides - hiophenes - heterocycles - Lawesson’s reagent - oxidation