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 = Autonomous University of Barcelona = Universidad Autónoma de Barcelona

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.

Domaines: Chimie de coordination

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, 2012, 77, pp.5056-5062. ⟨10.1021/jo3005149⟩. ⟨hal-00905051⟩