Mamboury, MathiasWang, QianZhu, Jieping2017-09-202017-09-202017-09-20201710.1002/chem.201703458https://infoscience.epfl.ch/handle/20.500.14299/140758WOS:000411033800011The palladium-catalyzed reaction of a-haloketones with isocyanides afforded -oxo-ketenimines through alpha-hydride elimination of the beta-oxo-imidoyl palladium intermediates. Reaction of these relatively stable alpha-oxo ketenimines with nucleophiles such as hydrazines, hydrazoic acid, amines, and Grignard reagent afforded pyrazoles, tetrazole, beta-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 alpha-oxo-ketenimines was initiated by nucleophilic addition to the carbonyl group.amidineheterocyclesisocyanidesketeniminepalladiumtext::journal::journal article::research article