Photocatalytic Intramolecular C–H Amination Using N‑Oxyureas as Nitrene Precursors

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...

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Veröffentlicht in:Organic letters 2020-08, Vol.22 (16), p.6360-6364
Hauptverfasser: Ivanovich, Ryan A, Polat, Dilan E, Beauchemin, André M
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02200