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Phosphine-free palladium-catalysed direct C2-arylation of benzothiophenes with aryl bromides

Abstract : Ligand-free Pd(OAc)2 was found to catalyse very efficiently the direct C2-arylation of benzothiophene derivatives under low catalyst concentration. The reaction can be performed employing as little as 0.5-0.1 mol % catalyst with electron-deficient and some electron-rich aryl bromides. The presence of a methyl or a formyl substituent at C3 of benzothiophene has a minor influence on the reactivity, and even a bromo substituents at C3 is tolerated. A wide variety of functional groups on the aryl bromide, such as nitrile, nitro, acetyl, formyl, ester, chloro, fluoro or trifluoromethyl has been employed.
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Submitted on : Wednesday, July 10, 2013 - 4:09:36 PM
Last modification on : Friday, July 10, 2020 - 4:05:49 PM
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Liqin Zhao, Christian Bruneau, Henri Doucet. Phosphine-free palladium-catalysed direct C2-arylation of benzothiophenes with aryl bromides. Tetrahedron, Elsevier, 2013, 69 (34), pp.7082-7089. ⟨10.1016/j.tet.2013.06.037⟩. ⟨hal-00843040v2⟩

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