Hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable C5-carbon of 3-substituted thiophenes. - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Beilstein Journal of Organic Chemistry Année : 2013

Hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable C5-carbon of 3-substituted thiophenes.

Résumé

The use of the congested aryl bromide 2-bromo-1,3-dichlorobenzene as coupling partner allows to modify the regioselectivity of the arylation of 3-substituted thiophene derivatives in favour of carbon C5. The coupling of this aryl bromide with a variety of 3-substituted thiophenes gave in all cases the desired 5-arylation products in moderate to good yields using only 0.5 mol % of a phosphine-free and air-stable palladium catalyst. Then, from these 5-arylthiophenes, a second palladium-catalysed C-H bond functionalization at C2 of the thiophene ring allows the synthesis of 2,5-diarylthiophenes with two different aryl units.

Domaines

Chimie

Dates et versions

hal-01114991 , version 1 (10-02-2015)

Identifiants

Citer

Rongwei Jin, Charles Beromeo Bheeter, Henri Doucet. Hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable C5-carbon of 3-substituted thiophenes.. Beilstein Journal of Organic Chemistry, 2013, 10, pp.1239-45. ⟨10.3762/bjoc.10.123⟩. ⟨hal-01114991⟩
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