Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group - Archive ouverte HAL Access content directly
Journal Articles Beilstein Journal of Organic Chemistry Year : 2016

Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group

Abstract

The use of a bromo-substituent as blocking group at the C2-position of 3-substituted thiophenes allows the regioselective introduction of aryl substituents at C5-position via Pd-catalysed direct arylation. With 1 mol % of a phosphine-free Pd catalyst, KOAc as the base and DMA as the solvent and various electron-deficient aryl bromides as aryl sources, C5-(hetero) arylated thiophenes were synthesized in moderate to high yields, without cleavage of the thienyl C-Br bond. Moreover, sequential direct thienyl C5-arylation followed by Pd-catalysed direct arylation or Suzuki coupling at the C2-position allows to prepare 2,5-di(hetero) arylated thiophenes bearing two different (hetero) aryl units in only two steps. This method provides a "green" access to arylated thiophene derivatives as it reduces the number of steps to prepare these compounds and also the formation of wastes.

Dates and versions

hal-01395475 , version 1 (10-11-2016)

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Mariem Brahim, Hamed Ben Ammar, Jean-François Soulé, Henri Doucet. Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group. Beilstein Journal of Organic Chemistry, 2016, 12, pp.2197--2203. ⟨10.3762/bjoc.12.210⟩. ⟨hal-01395475⟩
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