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

Abstract : 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.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01114991
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Submitted on : Tuesday, February 10, 2015 - 1:08:38 PM
Last modification on : Wednesday, April 7, 2021 - 3:18:07 PM

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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, Beilstein-Institut, 2013, 10, pp.1239-45. ⟨10.3762/bjoc.10.123⟩. ⟨hal-01114991⟩

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