Divergent Palladium‐ and Platinum‐Catalyzed Intramolecular Hydroamination/Hydroarylation of <i>O</i>‐Propargyl‐2‐aminophenols

Christodoulou, Michael S.; Giofrè, Sabrina; Broggini, Gianluigi; Mazza, Alberto; Sala, Roberto; Beccalli, Egle M.

doi:10.1002/ejoc.201801103

Cited by 3 publications

References 65 publications

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Copper(II)‐Catalyzed Aminohalogenation of Alkynyl Carbamates

et al. 2021

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A useful aminohalogenation reaction for the cyclization of O‐alkynyl carbamates under copper catalysis has been developed. N‐Halosuccinimides have been used as a halogen source. The intramolecular C−N bond formation occurs selectively affording haloalkylidene substituted heterocycles. Just in the case of α,α‐cyclohexyl‐substituted propargyl carbamate, the alkoxyhalogenation pathway was operative. The mechanism for the two alternative reaction pathways was investigated by modeling the corresponding transition states at the DFT level.

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Copper(II)‐Catalyzed Aminohalogenation of Alkynyl Carbamates

et al. 2021

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Six-Membered Ring Systems: With O and/or S Atoms

Santos¹,

Silva²

2020

Progress in Heterocyclic Chemistry

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This book and the individual contributions contained in it are protected under copyright by the Publisher (other than as may be noted herein). NoticesKnowledge and best practice in this field are constantly changing. As new research and experience broaden our understanding, changes in research methods, professional practices, or medical treatment may become necessary.Practitioners and researchers must always rely on their own experience and knowledge in evaluating and using any information, methods, compounds, or experiments described herein. In using such information or methods they should be mindful of their own safety and the safety of others, including parties for whom they have a professional responsibility.

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

et al. 2021

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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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Divergent Palladium‐ and Platinum‐Catalyzed Intramolecular Hydroamination/Hydroarylation of O‐Propargyl‐2‐aminophenols

Cited by 3 publications

References 65 publications

Copper(II)‐Catalyzed Aminohalogenation of Alkynyl Carbamates

Copper(II)‐Catalyzed Aminohalogenation of Alkynyl Carbamates

Six-Membered Ring Systems: With O and/or S Atoms

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

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