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Skhiri A, Ben Salem R, Soulé JF, et al. Reactivity of bromoselenophenes in palladium-catalyzed direct arylations. Beilstein J Org Chem. 2017;13:2862-2868doi: 10.3762/bjoc.13.278.
Skhiri, A., Ben Salem, R., Soulé, J. F., & Doucet, H. (2017). Reactivity of bromoselenophenes in palladium-catalyzed direct arylations. Beilstein journal of organic chemistry, 132862-2868. https://doi.org/10.3762/bjoc.13.278
Skhiri, Aymen, et al. "Reactivity of bromoselenophenes in palladium-catalyzed direct arylations." Beilstein journal of organic chemistry vol. 13 (2017): 2862-2868. doi: https://doi.org/10.3762/bjoc.13.278
Skhiri A, Ben Salem R, Soulé JF, Doucet H. Reactivity of bromoselenophenes in palladium-catalyzed direct arylations. Beilstein J Org Chem. 2017 Dec 22;13:2862-2868. doi: 10.3762/bjoc.13.278. eCollection 2017. PMID: 29564014; PMCID: PMC5753141.
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Beilstein J Org Chem. 2017 Dec 22;13:2862-2868. doi: 10.3762/bjoc.13.278. eCollection 2017.

Reactivity of bromoselenophenes in palladium-catalyzed direct arylations.

Beilstein journal of organic chemistry

Aymen Skhiri, Ridha Ben Salem, Jean-François Soulé, Henri Doucet

Affiliations

  1. Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, "Organométalliques: Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, France.
  2. Laboratoire de Laboratoire de Chimie Organique LR 17ES08, Université de Sfax, Faculté des Sciences de Sfax, Route de la Soukra km 4, 3038 Sfax, Tunisia.

PMID: 29564014 PMCID: PMC5753141 DOI: 10.3762/bjoc.13.278

Abstract

The reactivity of 2-bromo- and 2,5-dibromoselenophenes in Pd-catalyzed direct heteroarylation was investigated. From 2-bromoselenophene, 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

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