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Synthesis 2008(16): 2537-2542  
DOI: 10.1055/s-2008-1067181
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

New and Efficient Palladium(0)-Mediated Microwave-Assisted Direct C3 Alkenylation of Imidazo[1,2-a]pyridines

Jamal Koubachia,b, Saïd El Kazzoulia,b, Sabine Berteina-Raboin*a, Abderrahim Mouaddibb, Gérald Guillaumeta
a Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d’Orléans, BP 6759, 45067 Orléans Cedex 2, France
e-Mail: sabine.berteina-raboin@univ-orleans.fr;
b Faculté des Sciences et Techniques de Beni-Mellal, Université Soultan Moulay Sliman, BP 523, 23000 Beni-Mellal, Morocco
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Publikationsverlauf

Received 31 March 2008
Publikationsdatum:
17. Juli 2008 (online)

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Abstract

In this paper, we present the synthesis of 3-alkenylimidazo[1,2-a]pyridines in high to moderate yields by microwave direct palladium-catalyzed C-H alkenylation between bromoalkenes and imidazo[1,2-a]pyridines. The scope and limitation of the palladium(0)-catalyzed alkenylation method were investigated. Optimized conditions were successfully applied to a wide variety of imidazo[1,2-a]pyridine derivatives and bromoalkenes. The compatibility of the synthesis with the presence of a chloro substituent in the 6-position was investigated. The 6-chloroimidazo[1,2-a]pyridines were functionalized using Suzuki cross-coupling conditions to give polyfunctional compounds.

Key words

palladium-catalyzed coupling - alkenylation - imidazo[1,2-a]pyridines - microwave irradiation

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