1361978-89-3Relevant academic research and scientific papers
Practical azidation of 1,3-dicarbonyls
Harschneck, Tobias,Hummel, Sara,Kirsch, Stefan F.,Klahn, Philipp
supporting information; experimental part, p. 1187 - 1193 (2012/03/11)
An operationally simple, direct azidation of 1,3-dicarbonyl compounds has been developed. The reaction proceeds readily under ambient conditions using sodium azide and an iodine-based oxidant such as I2 or 2-iodoxybenzoic acid (IBX)-SO3K/NaI. In particular, the latter method, as a new and well-balanced oxidizing agent, shows excellent functional group tolerance and substrate scope and thus allows access to a variety of tertiary 2-azido and 2,2-bisazido 1,3-dicarbonyl compounds that would be more difficult to access by using traditional methods. Because the azide-containing products easily undergo 1,3-dipolar cycloaddition with alkynes, our report represents a novel route to analogues of sensitive complex molecules. Click into place! An operationally simple, direct azidation of 1,3-dicarbonyl compounds has been developed (see scheme). The reaction proceeds readily under ambient conditions using sodium azide and an iodine-based oxidant, such as I2 or 2-iodoxybenzoic acid (IBX)-SO3K/NaI. The oxidative methods show excellent functional-group tolerance and substrate scope and thus allow access to a variety of tertiary 2-azido and 2,2-bisazido 1,3-dicarbonyl compounds. Copyright
