title: Cleavage of 1,3-dicarbonyls through oxidative amidation.
abstract: A mild and convenient protocol for the oxidative cleavage of 1,3-diketone compounds is described. Under metal-free conditions, the method converts the 1,3-dicarbonyls into amides when treated with (nBu4N)N3and iodine in the presence of an amine at room temperature. Using this method, a range of 1,3-dicarbonyls with various structural motifs including sterically demanding substituents and ordinary functional groups were easily fragmented, and it is demonstrated that cyclic 1,3-dicarbonyls can be directly transformed into acyclic diamides through ring-opening. Initial mechanistic studies show that diazidation of the enol form is followed by nucleophilic substitution with the amine.
authors.affiliation: Organic Chemistry, Bergische Universität Wuppertal, Gaußstraße 20, 42119 Wuppertal, Germany. sfkirsch@uni-wuppertal.de.
authors.forename: Phillip
authors.initials: P
authors.lastname: Biallas
authors.forename: Andreas P
authors.initials: AP
authors.lastname: Häring
authors.forename: Stefan F
authors.initials: SF
authors.lastname: Kirsch