Reactivity of bromoselenophenes in palladium-catalyzed direct arylations

Aymen Skhiri (1, 2) , Ridha Ben Salem (2) , Jean-François Soulé (1) , Henri Doucet (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 Université de Sfax - University of Sfax

The reactivity of 2-bromo- and 2,5-dibromoselenophenes in Pd-catalyzed direct heteroarylation was investigated. From 2-bromo-selenophene, only the most reactive heteroarenes could be employed to prepare 2-heteroarylated selenophenes; whereas, 2,5-dibromoselenophene generally gave 2,5-di(heteroarylated) selenophenes in high yields using both thiazole and thiophene derivatives. Moreover, sequential catalytic C2 heteroarylation, bromination, catalytic C5 arylation reactions allowed the synthesis of unsymmetrical 2,5-di(hetero)arylated selenophene derivatives in three steps from selenophene.

Keywords: C-H bond activation; catalysis; heteroarenes; palladium; selenophene

Domains: Chemical Sciences

Aymen Skhiri, Ridha Ben Salem, Jean-François Soulé, Henri Doucet. Reactivity of bromoselenophenes in palladium-catalyzed direct arylations. Beilstein Journal of Organic Chemistry, 2017, 13, pp.2862-2868. ⟨10.3762/bjoc.13.278⟩. ⟨hal-01709524⟩