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Synthesis 2010(15): 2553-2566  
DOI: 10.1055/s-0029-1218814
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalysed Direct Heteroarylation of Bromobenzylacetamide Derivatives: A Simple Access to Heteroarylated Benzylamine Derivatives

Nouria Laidaouia,b, Abdellah Miloudib, Douniazad El Abed*b, Henri Doucet*a
a Institut Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes ‘Catalyse et Organometalliques’, Campus de Beaulieu, 35042 Rennes, France
Fax: +33(2)23236939; e-Mail: henri.doucet@univ-rennes1.fr;
b Laboratoire de Réactivité et Chimie Fine, Département de Chimie, Faculté des Sciences, Université d’Oran Es-Sénia, BP. 1524, EL M’naouer Oran 31100, Algeria
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Received 23 March 2010
Publikationsdatum:
15. Juni 2010 (online)

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Abstract

The palladium-catalysed direct arylation of bromobenzylacetamide derivatives using a wide variety of heteroaromatics gives a very simple access to heteroarylated benzylacetamides. 2-, 3- and 4-Bromobenzylacetamides present a very similar reactivity. In the presence of 2-subtituted furans, thiophenes, pyrroles, thia­zoles, or imidazoles a regioselective 5-arylation was observed. The reaction of benzoxazole gave the 2-arylated compounds; whereas 3,5-dimethylisoxazole gave the 4-arylated products. In most cases, the system using PdCl(C3H5)(dppb) as the catalyst, KOAc as the base, and DMAC as the solvent gave high yields of coupling products.

Key words

palladium - cross-coupling reaction - arylation - furans - thiophenes - pyrroles - thiazoles - imidazoles - benzoxazoles

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