Trimethylsilyl Azide Promoted Shono Oxidation of N,N-Dialkyl Amides

An alkoxylation of N,N-dialkyl amides by the Shono reaction has been developed that offers a simple and efficient way to access N-adjacent-carbon-substituted amides. TMSN3 plays an essential role in this transformation and permits the reaction to proceed with a broad substrate scope under mild conditions. This reaction proceeds at a lower current compared with the classical method and it affords the products in up to 91% yield. A possible mechanism is proposed based on control experiments.