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Practical azidation of 1,3-dicarbonyls.

Authors
  • Harschneck, Tobias
  • Hummel, Sara
  • Kirsch, Stefan F
  • Klahn, Philipp
Type
Published Article
Journal
Chemistry - A European Journal
Publisher
Wiley (John Wiley & Sons)
Publication Date
Jan 23, 2012
Volume
18
Issue
4
Pages
1187–1193
Identifiers
DOI: 10.1002/chem.201102680
PMID: 22189938
Source
Medline
License
Unknown

Abstract

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 I(2) or 2-iodoxybenzoic acid (IBX)-SO(3)K/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.

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