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- Title
α-Oxo-Ketenimines from Isocyanides and α-Haloketones: Synthesis and Divergent Reactivity.
- Authors
Mamboury, Mathias; Wang, Qian; Zhu, Jieping
- Abstract
The palladium-catalyzed reaction of α-haloketones with isocyanides afforded α-oxo-ketenimines through β-hydride elimination of the β-oxo-imidoyl palladium intermediates. Reaction of these relatively stable α-oxo-ketenimines with nucleophiles such as hydrazines, hydrazoic acid, amines, and Grignard reagent afforded pyrazoles, tetrazole, β-keto amidines, and enaminone, respectively, with high chemoselectivity. Whereas amines attack exclusively on the ketenimine functions, the formal [3+2] cycloaddition between N-monosubstituted hydrazines and α-oxo-ketenimines was initiated by nucleophilic addition to the carbonyl group.
- Subjects
KETENIMINES; PALLADIUM; ISOCYANIDES; HALOKETONES; NUCLEOPHILES
- Publication
Chemistry - A European Journal, 2017, Vol 23, Issue 52, p12744
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201703458