Selective α-oxidation of amides via visible-light-driven iron catalysis.
Org Biomol Chem
; 22(6): 1205-1212, 2024 Feb 07.
Article
em En
| MEDLINE
| ID: mdl-38224270
ABSTRACT
Hydroxyl radicals (ËOH) as one of the highly reactive species can react unselectively with a wide range of chemicals. The ËOH radicals are typically generated under harsh conditions. Herein, we report hydroxyl radical-induced selective N-α C(sp3)-H bond oxidation of amides under greener and mild conditions via an Fe(NO3)3·9H2O catalyst inner sphere pathway upon irradiation with a 30 W blue LED light strip (λ = 455 nm) using NaBrO3 as the oxidant. This protocol exhibited high chemoselectivity and excellent functional group tolerance. A preliminary mechanism investigation demonstrated that the iron catalyst afforded hydroxyl radicals via the visible-light-induced homolysis (VLIH) of iron complexes followed by a hydrogen atom transfer (HAT) process to realize this transformation.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2024
Tipo de documento:
Article