ArticleChemical science2023
1,2-Aminoxyalkylation of alkenes with alkyl iodides and TEMPONa through SET- and XAT-processes.
Article in Chemical science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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1 citing paper in PubMed.
- Harnessing redox properties of organic persistent radicals in SET-induced transformations.Beilstein journal of organic chemistry · 2026Review
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Abstract
1,2-Aminoxyalkylation of alkenes with alkyl iodides and TEMPONa in combination with an aryldiazonium salt as an XAT mediator is reported. Various primary, secondary and tertiary alkyl iodides engage as C-radical precursors in the 1,2-aminoxyalkylation with electrophilic alkenes as radical acceptors. The product alkoxyamines are readily transformed to the corresponding alcohols or ketones upon reduction or oxidation, respectively. Mechanistic investigations reveal that aryl radicals, generated through SET-reduction of the aryl diazonium salt with TEMPONa, engage in XAT from unactivated alkyl halides to give alkyl radicals that can add to alkenes. Trapping of the adduct radicals with TEMPO provides the 1,2-aminoxyalkylation products. Transition metals are not required for these transformations that are conducted under mild conditions. Perfluoroalkyl halides directly react with TEMPONa and an aryldiazonium salt as XAT-mediator is not required for alkene 1,2-aminoxyperfluoroalkylation.
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