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Palladium-Catalyzed Deaminative Cross-Coupling of Alkyl Nitroso Carbamates
Shashwati Paul1, Kanaram R Kumawat1, M Kevin Brown1
1Indiana University, Department of Chemistry, Bloomington, Indiana 47405, United States.
Abstract:
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 di- and tri-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.
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