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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...
The reaction of allyl ethyl carbonates with isocyanides in the presence of a catalytic amount of Pd(OAc)2 provided ketenimines through β‐hydride elimination of the allyl imidoylpalladium intermediates. The insertion of the isocyanide into the π‐allyl Pd complex proceeded via an unusual η1‐allyl Pd species. The resulting ketenimines were hydrolyzed to β,γ‐unsaturated carboxamides during purification...
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