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 by flash column chromatography on silica gel or converted in situ into 1,5-disubstituted tetrazoles by [3+2] cycloaddition with hydrazoic acid or trimethylsilyl azide.

[1] Dr. Guanyinsheng Qiu^†, Mathias Mamboury^†, Dr. Qian Wang and Prof. Dr. Jieping Zhu, Angew. Chem. Int. Ed. 2016, 55 ,15377 –15381

† These authors contributed equally.