ArticleJournal of the American Chemical Society2014
Redox-neutral α-oxygenation of amines: reaction development and elucidation of the mechanism.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed.
- Synthesis of tetrahydroisoquinoline-fused polycyclic heterocyclic skeletons via Vilsmeier-reagent promoted decarbonylative annulation.Communications chemistry · 2026Article
- Recent advances in bio-based polybenzoxazines as an interesting adhesive coating.RSC advances · 2023Review
- Synthesis of Polycyclic Isoindolines via α-C-H/N-H Annulation of Alicyclic Amines.Organic letters · 2022Article
- Cycloaddition of Huisgen 1,4-dipoles: synthesis and rapid epimerization of functionalized spiropyrido[2,1-RSC advances · 2021Article
- Article
- α-C-H/N-H Annulation of Alicyclic Amines via Transient Imines: Preparation of Polycyclic Lactams.Organic letters · 2021Article
- C-H Bond Functionalization of Amines: A Graphical Overview of Diverse Methods.SynOpen (2017) · 2021Article
- N-Activated 1,3-Benzoxazine Monomer as a Key Agent in Polybenzoxazine Synthesis.Macromolecules · 2020Article
- Design, synthesis and characterization of structurally dynamic cyclic N,S-acetals.Chemical communications (Cambridge, England) · 2020Article
- Redox-Annulations of Cyclic Amines withOrganic letters · 2020Article
- Traceless Redox-Annulations of Alicyclic Amines.SynOpen (2017) · 2020Article
- Redox-Annulations of Cyclic Amines with Electron-Deficient o-Tolualdehydes.Organic letters · 2019Article
- Computational investigation of the control of the thermodynamics and microkinetics of the reductive amination reaction by solvent coordination and a co-catalyst.RSC advances · 2018Article
- Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(spChemical science · 2018Article
- Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates.Organic letters · 2018Article
- Synthesis of Polycyclic Imidazolidinones via Amine Redox-Annulation.Organic letters · 2017Article
- Acetic Acid Promoted Redox Annulations with Dual C-H Functionalization.Organic letters · 2017Article
- Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Redox-Annulation of Cyclic Amines and β-Ketoaldehydes.Organic letters · 2016Article
- An Ugi Reaction Incorporating a Redox-Neutral Amine C-H Functionalization Step.Organic letters · 2016Article
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Authors and funding
7 authors.
Funding
Abstract
Cyclic secondary amines and 2-hydroxybenzaldehydes or related ketones react to furnish benzo[e][1,3]oxazine structures in generally good yields. This overall redox-neutral amine α-C-H functionalization features a combined reductive N-alkylation/oxidative α-functionalization and is catalyzed by acetic acid. In contrast to previous reports, no external oxidants or metal catalysts are required. Reactions performed under modified conditions lead to an apparent reductive amination and the formation of o-hydroxybenzylamines in a process that involves the oxidation of a second equivalent of amine. A detailed computational study employing density functional theory compares different mechanistic pathways and is used to explain the observed experimental findings. Furthermore, these results also reveal the origin of the catalytic efficiency of acetic acid in these transformations.
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