Abstract
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.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Amination
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Aniline Compounds / chemical synthesis
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Aniline Compounds / chemistry*
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Azo Compounds / chemical synthesis
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Azo Compounds / chemistry
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Catalysis
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Ketones / chemical synthesis*
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Ketones / chemistry
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Nitriles / chemical synthesis
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Nitriles / chemistry*
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Oxidation-Reduction
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Phthalimides / chemical synthesis
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Phthalimides / chemistry*
Substances
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Aniline Compounds
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Azo Compounds
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Ketones
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Nitriles
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Phthalimides
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phthalimide-N-oxyl
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N,N-dimethylaniline
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N-hydroxyphthalimide