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Reactivity of 3-(pyrrol-1-yl)thiophenes in Pd-catalysed direct arylations

Résumé : The regioselectivity of the Pd-catalysed direct arylation of 3-(pyrrol-1-yl)thiophene derivatives was investigated. Conditions allowing either the regioselective arylation at C2 or at C5 of the thiophene ring are reported. From methyl 3-(pyrrol-1-yl)thiophene-2-carboxylate using KOAc as the base, DMA as the solvent and only 1 mol % Pd(OAc)2 catalyst, the target 5-arylated thiophenes were obtained in moderate to good yields with a wide variety of aryl halides; whereas the use of 1-(4-methylthiophen-3-yl)-pyrrole affords the C2-arylated thiophenes. The sequential palladium catalysed 2,5-diheteroarylation of such 3-(pyrrol-1-yl)thiophene is also reported allowing the access to thiophenes bearing two different aryl units at C2 and C5. A pyrazole bearing an ester substituent at C4 and a pyrrole substituent at C5 was only arylated at C2 on the pyrrole ring.
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Submitted on : Wednesday, May 6, 2015 - 3:37:33 PM
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Imen Smari, Chiraz Youssef, Hamed Ben Ammar, Bechir Ben Hassine, Jean-François Soulé, et al.. Reactivity of 3-(pyrrol-1-yl)thiophenes in Pd-catalysed direct arylations. Tetrahedron, Elsevier, 2015, 71 (37), pp.6586-6593. ⟨10.1016/j.tet.2015.03.022⟩. ⟨hal-01149179⟩

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