Direct Synthesis of Enamides via Electrophilic Activation of Amides
Philipp Spieß, Martin Berger, Daniel Kaiser, Nuno Maulide
Abstract
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.
Topics & Concepts
ChemistryElectrophileDehydrogenationCombinatorial chemistrySubstrate (aquarium)Activator (genetics)Organic chemistryCatalysisBiochemistryGeologyGeneOceanographyAdvanced Synthetic Organic ChemistryAsymmetric Hydrogenation and CatalysisChemical Synthesis and Analysis