Photocatalytic Intramolecular C–H Amination Using <i>N</i>-Oxyureas as Nitrene Precursors
Ryan A. Ivanovich, Dilan E. Polat, André M. Beauchemin
Abstract
Nitrenes are remarkable high-energy chemical species that enable direct C-N bond formation, typically via controlled reactions of metal-stabilized nitrenes. Here, in contrast, the combined use of photocatalysis with careful engineering of the precursor enabled C-H amination forming imidazolidinones and related nitrogen heterocycles from readily accessible hydroxylamine precursors. Preliminary mechanistic results are consistent with the formation of free carbamoyl triplet nitrenes as reactive intermediates.
Topics & Concepts
NitreneAminationChemistryIntramolecular forcePhotocatalysisPhotochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions