Conditions for the Palladium-Catalysed Direct 2-Arylation of 3-Bromobenzo[b]thiophene Tolerant of the Benzothienyl Carbon-Bromine Bond - Université de Rennes Access content directly
Journal Articles Synthesis: Journal of Synthetic Organic Chemistry Year : 2015

Conditions for the Palladium-Catalysed Direct 2-Arylation of 3-Bromobenzo[b]thiophene Tolerant of the Benzothienyl Carbon-Bromine Bond

Abstract

Phosphine-free palladium(II) acetate catalyst was found to promote the direct 2-arylation of 3-bromobenzo[b]thiophene without cleavage of the benzothienyl carbon-bromine bond, allowing the synthesis of 2-aryl-3-bromobenzo[b]thiophenes in only one step. The best results were generally obtained using a low loading of the palladium catalyst (0.5 mol%), quite low reaction temps. (80-120 °C) and short reaction times (0.5-2 h). The reaction proceeds with electron-deficient para-, meta- and ortho-substituted aryl bromides and also with heteroaryl bromides. The benzothienyl carbon-bromine bond has been profitably employed for further palladium-catalyzed functionalisations. This strategy allows the straightforward synthesis of 2,3-di(hetero)arylated benzo[b]thiophenes with two different (hetero)aryl units via sequential catalytic arylations.
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Dates and versions

hal-01188188 , version 1 (16-12-2015)

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Imen Smari, Hamed Ben Ammar, Bechir Ben Hassine, Jean-François Soulé, Henri Doucet. Conditions for the Palladium-Catalysed Direct 2-Arylation of 3-Bromobenzo[b]thiophene Tolerant of the Benzothienyl Carbon-Bromine Bond. Synthesis: Journal of Synthetic Organic Chemistry, 2015, 47 (21), pp.3354-3362. ⟨10.1055/s-0034-1378733⟩. ⟨hal-01188188⟩
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