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Reactivity of bromoselenophenes in palladium-catalyzed direct arylations

Abstract : The reactivity of 2-bromo- and 2,5-dibromoselenophenes in Pd-catalyzed direct heteroarylation was investigated. From 2-bromo-selenophene, only the most reactive heteroarenes could be employed to prepare 2-heteroarylated selenophenes; whereas, 2,5-dibromoselenophene generally gave 2,5-di(heteroarylated) selenophenes in high yields using both thiazole and thiophene derivatives. Moreover, sequential catalytic C2 heteroarylation, bromination, catalytic C5 arylation reactions allowed the synthesis of unsymmetrical 2,5-di(hetero)arylated selenophene derivatives in three steps from selenophene.
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Aymen Skhiri, Ridha Ben Salem, Jean-François Soulé, Henri Doucet. Reactivity of bromoselenophenes in palladium-catalyzed direct arylations. Beilstein Journal of Organic Chemistry, Beilstein-Institut, 2017, 13, pp.2862-2868. ⟨10.3762/bjoc.13.278⟩. ⟨hal-01709524⟩

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