Switchable Oxidative Reactions of N-allyl-2-Aminophenols: Palladium-Catalyzed Alkoxyacyloxylation vs an Intramolecular Diels–Alder Reaction

[Image: see text] The Pd(II)-catalyzed reaction of N-allyl-2-aminophenols in the presence of PhI(OCOR)(2) as the oxidant resulted in an alkoxyacyloxylation process, with the formation of functionalized dihydro-1,4-benzoxazines. The reaction performed in the absence of palladium catalyst switched to...

Descripción completa

Detalles Bibliográficos
Autores principales: Giofrè, Sabrina, Keller, Manfred, Lo Presti, Leonardo, Beccalli, Egle M., Molteni, Letizia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8524420/
https://www.ncbi.nlm.nih.gov/pubmed/34570517
http://dx.doi.org/10.1021/acs.orglett.1c02539
Descripción
Sumario:[Image: see text] The Pd(II)-catalyzed reaction of N-allyl-2-aminophenols in the presence of PhI(OCOR)(2) as the oxidant resulted in an alkoxyacyloxylation process, with the formation of functionalized dihydro-1,4-benzoxazines. The reaction performed in the absence of palladium catalyst switched to an intramolecular Diels–Alder reaction (IMDA) pathway, which was the result of an oxidative dearomatization of the 2-aminophenol, nucleophilic addition, and Diels–Alder reaction cascade, highlighting the role of the oxidant as both a nucleophilic donor and an oxidizing agent.

Ejemplares similares