Iodine(III)-Mediated Diazidation and Azido-oxyamination of Enamides.
In this study we demonstrate that the combination of bis(tert-butylcarbonyloxy)iodobenzene and lithium azide in acetonitrile allows the diazidation of various enamide substrates. The azido-oxyamination of the same substrates can be carried out in the presence of 2,2,6,6-tetramethylpiperidine N-oxide (TEMPO). Control experiments strongly suggest that this latter process occurs through a shift in nature of the in situ generated electrophilic species from a radical to a cation. Finally, the versatility of the novel compounds synthesized was also assessed by running various selective reactions on them.
Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, LabEx LERMIT, Avenue de la Terrasse, 91198 Gif-sur-Yvette (France), Fax: (+33) 1-6907-7247.
Sophie
S
Nocquet-Thibault
Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, LabEx LERMIT, Avenue de la Terrasse, 91198 Gif-sur-Yvette (France), Fax: (+33) 1-6907-7247.
Anita
A
Rayar
Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, LabEx LERMIT, Avenue de la Terrasse, 91198 Gif-sur-Yvette (France), Fax: (+33) 1-6907-7247.
Pascal
P
Retailleau
Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, LabEx LERMIT, Avenue de la Terrasse, 91198 Gif-sur-Yvette (France), Fax: (+33) 1-6907-7247. kevin.cariou@cnrs.fr.
Kevin
K
Cariou
Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, LabEx LERMIT, Avenue de la Terrasse, 91198 Gif-sur-Yvette (France), Fax: (+33) 1-6907-7247. robert.dodd@cnrs.fr.
Robert H
RH
Dodd
azides; enamides; hypervalent iodine; tempo; umpolung