Palladium-Catalyzed Deaminative Cross-Coupling of Alkyl Nitroso Carbamates

A palladium-catalyzed deaminative Heck-type coupling of alkyl nitroso carbamates, prepared from commercially available alkyl amines and aryl bromides, is reported. The reaction leads to the synthesis of <i>di</i>- and <i>tri</i>-substituted alkene products. Functional group tolerance was demonstrated in several examples. Use of triethylsilane under the reaction conditions also afforded products of a formal (Csp³)-(Csp²) cross-coupling. In addition to presenting a useful coupling protocol, this study also introduces nitroso carbamates into the realm of Pd-catalyzed cross-coupling.