title: Practical azidation of 1,3-dicarbonyls.
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.
authors.affiliation: Department of Chemistry, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany.
authors.forename: Tobias
authors.initials: T
authors.lastname: Harschneck
authors.forename: Sara
authors.initials: S
authors.lastname: Hummel
authors.forename: Stefan F
authors.initials: SF
authors.lastname: Kirsch
authors.forename: Philipp
authors.initials: P
authors.lastname: Klahn
mesh_terms: D001386:Azides / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D057930:Click Chemistry; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*
chemical_list: D001386:Azides; D002244:Carbon; D007455:Iodine; D010100:Oxygen; D004121:Dimethyl Sulfoxide