Organic Letters · 2014 · 66 citations · 69 references
Natural SciencesChemistryMedicinal ChemistryBiocatalysisCatalysisOrganic ChemistryBiomimetic SynthesisHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsMetal CatalysisBiomimetic OxidationCopper CatalysisCopper-catalyzed CouplingCopper-catalyzed OxidationHeterocycle FunctionalizationKetonesLuciferin Chemistry
A direct one-pot Cu-catalyzed biomimetic oxidation of methyl ketones to pharmaceutically important N-heterocyclic amides is reported. The scope of the method is broad, scalable, and mild, and the reaction is tolerant with various acid, base sensitive functionalities with multiple heteroatoms and aryl halides. The extensive mechanistic studies suggest that this reaction follows the Luciferin-Luciferase-like pathway.
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