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Synthesis of palladium-bidentate complex and its application in Sonogashira and Suzuki coupling reactions

Boumediene Haddad, Didier Villemin, and El-habib Belarbi

Department of Chemistry, Synthesis and Catalysis Laboratory LSCT, Tiaret University, Tiaret, Algeria

 

E-mail: didier.villemin@ensicaen.fr

Abstract: A new palladium-bidentate complex [m-C6H4(CH2ImMe)2(PdCl2)] (III) was prepared in two steps. In the first step, [m-C6H4(CH2ImMeAgCl)2] (II) (Im = imidazole moiety) was obtained by reacting imidazolium salt [m-C6H4(CH2ImMe)2]Cl2 (I) (prepared by quaternisation of Nmethylimidazole with 1,3-bis(chloromethyl)benzene) and Ag2O in CH2Cl2. In the next step, treatment of (II) with Pd(CH3CN)2Cl2 afforded complex III which was evaluated for its catalytic activity for C-C bond-formation reactions by examining the coupling reaction of 3-iodoanisole with phenylacetylene in the Sonogashira reaction. In addition, 3-methoxybiphenyls were obtained with good to excellent yields by Suzuki coupling reactions of 3-iodoanisole with phenylboronic acids or phenylborates salts in the presence of this complex.

Keywords: palladium-bidentate complex – N-heterocyclic carbene (NHC) – Sonogashira reaction – Suzuki coupling – imidazolium salt

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-013-0489-3

 

Chemical Papers 68 (5) 656–661 (2014)

Wednesday, May 22, 2024

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