ArticleThe Journal of organic chemistry2024
Mechanism of Iron-Catalyzed Oxidative α-Amination of Ketones with Sulfonamides.
Article in The Journal of organic chemistry, 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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Who cites it
3 citing papers in PubMed.
- Nitrosonium Tetrafluoroborate-Promoted α,α-Diacetoxylation of Aryl Methyl Ketones.The Journal of organic chemistry · 2026Article
- Oxidative benzylic C(spChemical science · 2025Article
- Direct, Convergent α-Amidation of β-Keto Esters via Nickelocene Catalysis.Organic letters · 2025Article
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Authors and funding
6 authors.
Funding
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Abstract
We report the mechanism of the iron-catalyzed oxidative α-amination of ketones with sulfonamides. Using linear free energy relationships, competition experiments, and identification of reaction intermediates, we have found that the mechanism of this reaction proceeds through rate-limiting electron transfer to 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) from an iron enolate in the process of forming an α-DDQ adduct. The adduct then serves as the electrophile for substitution with sulfonamide nucleophiles, accelerated by iron and additional DDQ. This mechanistic study rules out formation of an α-carbocation intermediate and purely radical mechanistic hypotheses.
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Registered trials
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