Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Inorganic Chemistry Année : 2014

Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization

Résumé

New chiral nitroxides based on the imidazolidin-4-one skeleton, and the corresponding hydroxylamines, have been prepared from cyclic nitrones by a straightforward reaction sequence. They were evaluated as catalysts in the aerobic oxidation of benzyl alcohol using different co-catalysts. Both the imidazolidinone nitroxides and hydroxylamines were proven to catalyze the reaction, with the ring substituent having an effect depending on the co-catalytic system. In some cases, rapid oxidation to benzaldehyde was accomplished at room temperature under an atmospheric O2 pressure. Moreover, atroposelective desymmetrization was achieved during the aerobic oxidation of a diol catalyzed by an enantiopure imidazolidinone nitroxide. Finally, the electrochemical behavior of the new hydroxylamines and nitroxides was investigated by cyclic voltammetry, which gave insights into the observed catalytic properties.

Domaines

Chimie organique

Dates et versions

hal-01080412 , version 1 (05-11-2014)

Identifiants

Citer

Marta Carbó López, Guy Royal, Christian Philouze, Pierre Y. Chavant, Véronique Blandin. Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization. European Journal of Inorganic Chemistry, 2014, 2014 (22), pp.4884. ⟨10.1002/ejoc.201402324⟩. ⟨hal-01080412⟩
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