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. 2014 Dec 9:10:2912-9.
doi: 10.3762/bjoc.10.309. eCollection 2014.

Palladium-catalyzed 2,5-diheteroarylation of 2,5-dibromothiophene derivatives

Fatma Belkessam  1 , Aidene Mohand  2 , Jean-François Soulé  3 , Abdelhamid Elias  1 , Henri Doucet  3
Affiliations

Palladium-catalyzed 2,5-diheteroarylation of 2,5-dibromothiophene derivatives

Fatma Belkessam et al. Beilstein J Org Chem. .

Abstract

Conditions allowing the one pot 2,5-diheteroarylation of 2,5-dibromothiophene derivatives in the presence of palladium catalysts are reported. Using KOAc as the base, DMA as the solvent and only 0.5-2 mol % palladium catalysts, the target 2,5-diheteroarylated thiophenes were obtained in moderate to good yields and with a wide variety of heteroarenes such as thiazoles, thiophenes, furans, pyrroles, pyrazoles or isoxazoles. Moreover, sequential heteroarylation reactions allow the access to 2,5-diheteroarylated thiophenes bearing two different heteroaryl units.

Keywords: C–H bond activation; aryl halides; catalysis; direct arylation; heteroarenes; palladium.

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Figures

Figure 1
Figure 1
2,2':5',2"-Terthiophene.
Scheme 1
Scheme 1
Palladium-catalyzed direct arylation using 2,5-dibromothiophene and 2-ethyl-4-methylthiazole as coupling partners.
Scheme 2
Scheme 2
Reactivity of 2,5-dibromothiophene with different heteroarenes.
Scheme 3
Scheme 3
Reactivity of 2,5-dibromo-3-methylthiophene with different heteroarenes.
Scheme 4
Scheme 4
Sequential diheteroarylation of 2,5-dibromothiophene.
Scheme 5
Scheme 5
Sequential diheteroarylation of 2,5-dibromothiophene.
Scheme 6
Scheme 6
Heteroarylation of 2-bromothiophene.
Scheme 7
Scheme 7
Reactivity of 4,7-dibromobenzothiadiazole.
See this image and copyright information in PMC

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