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Reactivity of benzofuran and benzothiophene in palladium-catalysed direct C2,C3-diarylations

Abstract : The Pd-catalysed one pot direct diarylation of benzofuran and benzothiophene at both C2- and C3-positions was studied. In the presence of electron-deficient aryl bromides, the diarylation of benzofuran proceeded in good yields; whereas, with benzothiophene moderate yields were generally obtained, as the C3-position exhibits a poor reactivity. In order to obtain 2,3-diarylated benzothiophenes, its sequential arylation was examined. We found that the C3-arylation of benzothiophene followed by its C2-arylation provides a reliable methodology for the access to 2,3-diarylbenzothiophenes.
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Submitted on : Friday, October 13, 2017 - 9:28:00 AM
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Karima Si Larbi, Safia Djebbar, Jean-François Soulé, Henri Doucet. Reactivity of benzofuran and benzothiophene in palladium-catalysed direct C2,C3-diarylations. Journal of Organometallic Chemistry, Elsevier, 2017, 843, pp.32-39. ⟨10.1016/j.jorganchem.2017.05.029⟩. ⟨hal-01559209⟩

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