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Synthesis 2005(14): 2373-2378
DOI: 10.1055/s-2005-870014
DOI: 10.1055/s-2005-870014
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Diarylamines in the Thiophene Series by Buchwald-Hartwig Coupling
Further Information
Received
8 March 2005
Publication Date:
13 July 2005 (online)
Publication History
Publication Date:
13 July 2005 (online)
Abstract
We describe here the palladium-catalyzed amination of polysubstituted bromothiophenes under mild conditions (using Cs2CO3 as base). Anilines bearing electron-donating groups gave good results whereas anilines with electron-withdrawing substituents required greater catalyst loadings and gave lower yields.
Key words
palladium catalysis - amination - bromothiophenes - diarylamines
- Reviews :
-
1a
Hartwig JF. Synlett 1997, 329 -
1b
Yang BH.Buchwald SL. J. Organomet. Chem. 1999, 576: 125 - Examples for the amination of other heteroaryl halides for coupling of halopyridines see:
-
2a
Wagaw S.Buchwald SL. J. Org. Chem. 1996, 61: 7240 -
2b
Jonckers THM.Maes BUW.Lemière GLF.Dommisse R. Tetrahedron 2001, 57: 7027 -
2c For coupling of chloroquinoline see:
Jonckers THM.Maes BUW.Lemière GLF.Rombouts G.Pieters L.Haemers A.Dommisse R. Synlett 2003, 615 -
2d For coupling of bromopyrrole see:
Castellote I.Vaquero JJ.Alvarez-Builla J. Tetrahedron Lett. 2004, 45: 769 -
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References
Aminothiophenes were synthesized as described in ref. 7.