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Cobalt-Catalyzed Vinylation of Aromatic Halides Using beta-Halostyrene: Experimental and DFT Studies

Aurelien Moncomble 1 Pascal Le Floch 1 Agusti Lledós 2 Corinne Gosmini 1
1 DCPH - Laboratoire Hétéroéléments et Coordination
2 UAB - Universitat Autònoma de Barcelona
Abstract : A new protocol for the direct cobalt-catalyzed vinylation of aryl halides using β-halostyrene has been developed in order to form functionalized stilbenes. A variety of aromatic halides featuring different reactive group were employed. This method proceeded smoothly with a total retention of the double bond configuration in the presence of triphenylphosphine as ligand. Preliminary DFT calculations riphenylphosphine as ligand. Preliminary DFT calculations rationnalize these results and proposed a reaction pathway in agreement with the experimental conditions. This procedure offers a new route to the stereoselective synthesis of stilbenes.
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https://hal-polytechnique.archives-ouvertes.fr/hal-00905051
Contributor : Francoise Girard <>
Submitted on : Friday, November 15, 2013 - 5:07:35 PM
Last modification on : Tuesday, November 24, 2020 - 4:40:04 PM

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Aurelien Moncomble, Pascal Le Floch, Agusti Lledós, Corinne Gosmini. Cobalt-Catalyzed Vinylation of Aromatic Halides Using beta-Halostyrene: Experimental and DFT Studies. Journal of Organic Chemistry, American Chemical Society, 2012, 77, pp.5056-5062. ⟨10.1021/jo3005149⟩. ⟨hal-00905051⟩

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