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

Nouria Laidaoui; Abdellah Miloudi; Douniazad El Abed; Henri Doucet

doi:10.1055/s-0029-1218814

PAPER

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

Nouria Laidaoui^a,b, Abdellah Miloudi^b, 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

Abstract

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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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