Tetrabutylammonium iodide-catalyzed oxidative α-azidation of ß-ketocarbonyl compounds using sodium azide.
Beilstein J Org Chem
; 20: 1510-1517, 2024.
Article
em En
| MEDLINE
| ID: mdl-38978746
ABSTRACT
We herein report the oxidative α-azidation of carbonyl compounds by using NaN3 in the presence of dibenzoyl peroxide catalyzed by tetrabutylammonium iodide (TBAI). By utilizing these readily available bulk chemicals a variety of cyclic ß-ketocarbonyl derivatives can be efficiently α-azidated under operationally simple conditions. Control experiments support a mechanistic scenario involving in situ formation of an ammonium hypoiodite species which first facilitates the α-iodination of the pronucleophile, followed by a phase-transfer-catalyzed nucleophilic substitution by the azide. Furthermore, we also show that an analogous α-nitration by using NaNO2 under otherwise identical conditions is possible as well.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Beilstein J Org Chem
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
Áustria