Direct Synthesis of Enamides via Electrophilic Activation of Amides

A novel, one-step N-dehydrogenation of amides to enamides is reported. This reaction employs the unlikely combination of LiHMDS and triflic anhydride, which serves as both the electrophilic activator and the oxidant, and is characterized by its simple setup and broad substrate scope. The synthetic utility of the formed enamides was readily demonstrated in a range of downstream transformations.

Automated summary

This study reports a novel and simple reaction for the one-step N-dehydrogenation of amides to enamides, using the unlikely combination of LiHMDS and triflic anhydride. The formed enamides demonstrate broad substrate scope and synthetic utility in downstream transformations.