ArticleJACS Au2024
Redox-Neutral Umpolung Synthesis of α-Functionalized Amides.
Article in JACS Au, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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3 citing papers in PubMed.
- Influence of N-Functionalization of Amiridine on the Biological Activity of Its Conjugates as Multitarget Agents for Potential Treatment of Alzheimer's Disease.ChemMedChem · 2026Article
- Synthetic Applications of Hydroxamic Acids and Their Derivatives in Organic Chemistry.ACS organic & inorganic Au · 2026Review
- Solvent-controlled, chemodivergent oxidative anionic Fries rearrangement ofChemical science · 2026Article
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5 authors.
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Abstract
α-Heteroatom-substituted amides are useful as both targets and intermediates but are challenging to synthesize via conventional enolate chemistry. Herein, we describe a general and unified umpolung procedure to prepare α-heteroatom-functionalized secondary amides with various heteroatom-based nucleophiles under redox-neutral conditions. This transformation is a formal oxidation state reshuffle process from -N to -C in the hydroxamate, thereby achieving the umpolung α-heterofunctionalization of carbonyl groups without external oxidants. Regulated by the reshuffle mechanism, functionalization exclusively occurs at the α-position of the hydroxamate and precisely affords the α-functionalized amide with reliable predictability even in complex settings. Density functional theory studies support that soft enolization enabled by Mg
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