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Synthesis 2005(4): 610-616  
DOI: 10.1055/s-2005-861804
PAPER
© Georg Thieme Verlag Stuttgart · New York

Stille Coupling of 2-Diarylaminothiophenes with Mono- and Di­bromo(het)arylenes

Ahcene Tabet, Horst Hartmann*
Department of Chemistry, University of Applied Sciences, Geusaer Str., 06217 Merseburg, Germany
Fax: +49(3461)462192; e-Mail: Horst.Hartmann@cui.fh-merseburg.de;
Further Information

Publication History

Received 10 August 2004
Publication Date:
09 February 2005 (online)

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Abstract

N,N-Diaryl-substituted 2-aminothiophenes 3 have been transformed by reaction with several bromobenzenes 5 and 2-bromothiophenes 6 in a palladium catalysed cross-coupling reaction, via 2-(N,N-diarylamino)-5-stannyl-thiophenes 4, into N,N-diaryl-substituted 2-amino-5-phenylthiophenes 7 and 5-amino-2,2′-bi­thiophenes 9 as well as into N,N′-peraryl-substituted 5,5′-diamino-2,2′-bithiophenes 8 and their phenylene and thienylene homologues 10-13.

Key words

cross-coupling - heterocycles - metalations - palladium - Stille reaction