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Synthesis 2002(17): 2487-2489
DOI: 10.1055/s-2002-35620
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

A Versatile Route to N,N′-(Peraryl)substituted 5,5′-Diamino-2,2′-bithiophenes

Peter Gerstner, Dirk Rohde, Horst Hartmann*
Fachhochschule Merseburg, 06217 Merseburg, Germany
Fax: +49(346)1462192; e-Mail: Horst.Hartmann@cui.fh-merseburg.de;
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Publication History

Received 19 June 2002
Publication Date:
20 November 2002 (online)

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Abstract

The reaction of 5,5′-dibromo-2,2′-bithiophene with di­arylamines in the presence of palladium acetate/tris-(t-butyl)phosphine as catalyst or by a titanium tetrachloride mediated oxidation of 2-(N,N-diarylamino)thiophenes has yielded a series of new N,N′-perarylated 5,5-diamino-2,2′-bithiophenes. These are electron-rich compounds with a low oxidation potential and have a high tendency to form amorphous glasses.

Key words

aminations - 5,5′-diamino-2,2′-bithiophenes - nucleophilic substitution - palladium catalysis - sulfur heterocycles