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Article Dans Une Revue Chemistry - A European Journal Année : 2015

Iodine(III)-mediated diazidation and azido-oxyamination of enamides

Résumé

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 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.

Domaines

Chimie organique
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Dates et versions

hal-03026966 , version 1 (26-11-2020)

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Citer

S. Nocquet-Thibault, Anita Marie Rayar, Pascal ́ Retailleau, Kevin Cariou, Robert Dodd. Iodine(III)-mediated diazidation and azido-oxyamination of enamides. Chemistry - A European Journal, 2015, 21 (40), pp.14205-14210. ⟨10.1002/chem.201501782⟩. ⟨hal-03026966⟩
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