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...

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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
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author Giofrè, Sabrina
Keller, Manfred
Lo Presti, Leonardo
Beccalli, Egle M.
Molteni, Letizia
author_facet Giofrè, Sabrina
Keller, Manfred
Lo Presti, Leonardo
Beccalli, Egle M.
Molteni, Letizia
author_sort Giofrè, Sabrina
collection PubMed
description [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.
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spelling pubmed-85244202021-10-19 Switchable Oxidative Reactions of N-allyl-2-Aminophenols: Palladium-Catalyzed Alkoxyacyloxylation vs an Intramolecular Diels–Alder Reaction Giofrè, Sabrina Keller, Manfred Lo Presti, Leonardo Beccalli, Egle M. Molteni, Letizia Org Lett [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. American Chemical Society 2021-09-27 2021-10-15 /pmc/articles/PMC8524420/ /pubmed/34570517 http://dx.doi.org/10.1021/acs.orglett.1c02539 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Giofrè, Sabrina
Keller, Manfred
Lo Presti, Leonardo
Beccalli, Egle M.
Molteni, Letizia
Switchable Oxidative Reactions of N-allyl-2-Aminophenols: Palladium-Catalyzed Alkoxyacyloxylation vs an Intramolecular Diels–Alder Reaction
title Switchable Oxidative Reactions of N-allyl-2-Aminophenols: Palladium-Catalyzed Alkoxyacyloxylation vs an Intramolecular Diels–Alder Reaction
title_full Switchable Oxidative Reactions of N-allyl-2-Aminophenols: Palladium-Catalyzed Alkoxyacyloxylation vs an Intramolecular Diels–Alder Reaction
title_fullStr Switchable Oxidative Reactions of N-allyl-2-Aminophenols: Palladium-Catalyzed Alkoxyacyloxylation vs an Intramolecular Diels–Alder Reaction
title_full_unstemmed Switchable Oxidative Reactions of N-allyl-2-Aminophenols: Palladium-Catalyzed Alkoxyacyloxylation vs an Intramolecular Diels–Alder Reaction
title_short Switchable Oxidative Reactions of N-allyl-2-Aminophenols: Palladium-Catalyzed Alkoxyacyloxylation vs an Intramolecular Diels–Alder Reaction
title_sort switchable oxidative reactions of n-allyl-2-aminophenols: palladium-catalyzed alkoxyacyloxylation vs an intramolecular diels–alder reaction
url 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
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