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

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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.

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

    Boumediene Haddad & El-habib Belarbi

  2. Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN et Université de Caen Basse-Normandie, 14050, Caen, France

    Boumediene Haddad & Didier Villemin

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  1. Boumediene Haddad
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Correspondence to Didier Villemin.

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Haddad, B., Villemin, D. & Belarbi, Eh. Synthesis of palladium-bidentate complex and its application in Sonogashira and Suzuki coupling reactions. Chem. Pap. 68, 656–661 (2014). https://doi.org/10.2478/s11696-013-0489-3

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