Photoinduced Metalation of Nonactivated C-Cl Bonds with Samarium Diiodide: Synthesis of Alkenes with High (Z)-Selectivity through β-Elimination Reactions
José M. Concellón,* Humberto Rodríguez-Solla, Carmen Simal and Mónica Huerta
*Departamento de Química Orgánica e Inorgánica, Facultad de Química,
Universidad de Oviedo, Julián Clavería, 8, 33006, Oviedo, Spain, Email: jmcg
uniovi.es
J. M. Concellon, H. Rodriguez-Solla, C. Simal, M. Huerta, Org. Lett., 2005, 7, 5833-5835.
DOI: 10.1021/ol0523392
Abstract
Samarium diiodide promotes a photoinduced metalation of nonactivated C-Cl bonds of O-acetyl chlorohydrins and a β-elimination which affords alkenes with total or high stereoselectivity.
see article for more examples
A Convenient Samarium-Promoted Synthesis of Aliphatic (E)-Nitroalkenes under Mild Conditions
J. M. Concellón, P. L. Bernad, H. Rodríguez-Solla, C. Concellón, J. Org. Chem., 2007, 72, 5451-5423.
Key Words
syn Eliminations, anti Eliminations, Samarium Diiodide
ID: J54-Y2005-2170
