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DOI: 10.1055/s-0029-1218814
Palladium-Catalysed Direct Heteroarylation of Bromobenzylacetamide Derivatives: A Simple Access to Heteroarylated Benzylamine Derivatives
Publication History
Publication Date:
15 June 2010 (online)
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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