Metal-free C(sp(3))-H functionalization: oxidative carbo-oxygenation of α-diazo carbonyls via radical dediazotization

Metal-free C(sp(3))-H functionalization: oxidative carbo-oxygenation of α-diazo carbonyls via radical dediazotization

A novel three-component carbo-oxygenation of α-diazo carbonyls for flexible synthesis of unprecedented α-aminooxy-β-amino ketones has been established through metal-free C(sp(3))-H functionalization from readily accessible N,N-dimethylanilines and N-hydroxyphthalimide. The reaction pathway involves...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (29), p.5144-5147
Hauptverfasser: Wang, Nan-Nan, Hao, Wen-Juan, Zhang, Tian-Shu, Li, Guigen, Wu, Ya-Nan, Tu, Shu-Jiang, Jiang, Bo
Format: Artikel
Sprache:eng
Schlagworte:
Accessibility
Amination
Aniline Compounds - chemical synthesis
Aniline Compounds - chemistry
Azo Compounds - chemical synthesis
Azo Compounds - chemistry
Bonding
Carbon-carbon composites
Carbonyls
Catalysis
Coupling
Ketones
Ketones - chemical synthesis
Ketones - chemistry
Nitriles - chemical synthesis
Nitriles - chemistry
Oxidation-Reduction
Phthalimides
Phthalimides - chemical synthesis
Phthalimides - chemistry
Radicals
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Zusammenfassung:A novel three-component carbo-oxygenation of α-diazo carbonyls for flexible synthesis of unprecedented α-aminooxy-β-amino ketones has been established through metal-free C(sp(3))-H functionalization from readily accessible N,N-dimethylanilines and N-hydroxyphthalimide. The reaction pathway involves an in situ-generated phthalimide N-oxyl radical-triggered dediazotization/radical coupling sequence, leading to C-O and C-C bond formation.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc00816j