4.6 Article

Practical Azidation of 1,3-Dicarbonyls

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 18, 期 4, 页码 1187-1193

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201102680

关键词

azides; chemoselectivity; click chemistry; hypervalent compounds; oxidation

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  1. Deutsche Forschungsgemeinschaft (DFG)
  2. Fonds der Chemischen Industrie (FCI)

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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.

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