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Paper | Regular issue | Vol 100, No. 5, 2020, pp.747-767
Published online, 31st March, 2020
DOI: 10.3987/COM-20-14234
Copper-catalyzed β-Iodovinylation of Azole and Pyrrole Derivatives

Simon Ricard, François Ladouceur, Guillaume Couture, and Benoit Daoust*

*Department of Chemistry, Biochemistry and Physics, University of Quebec in Trois-Rivieres, CP. 500, Trois-Rivieres, Quebec, Canada


Herein is described an efficient copper-catalyzed synthesis of β-iodovinyl-azole and β-iodovinyl-pyrrole derivatives using (E)-1,2-diiodoethene which was efficiently applied to azole and pyrrole derivatives in both organic and hydro-organic medium to afford the corresponding β-iodovinylated adducts in up to excellent yields with complete stereocontrol. These nitrogenated vinyl iodides can be further functionalized into disubstituted olefins through various metal catalyzed coupling reactions.