Abstract
A novel fluorous-tagged ammonia surrogate has been synthesized and its application to the synthesis of anilines by Buchwald-Hartwig palladium-catalyzed amidation-hydrolysis protocol is described. Primary anilines were obtained in moderate to good yields after a sequence of two reaction steps involving fluorous separation techniques for their purification. Preliminary results indicate that N-substituted anilines can also be obtained using just N-substituted-FBoc carbamates as the nitrogen source.
MeSH terms
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Amination
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Ammonia / chemistry
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Aniline Compounds / chemical synthesis*
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Aniline Compounds / chemistry
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Benzophenones / chemistry
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Carbamates / chemical synthesis
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Carbamates / chemistry*
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Catalysis
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Formic Acid Esters / chemical synthesis
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Formic Acid Esters / chemistry
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Hydrocarbons, Aromatic / chemistry*
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Hydrocarbons, Brominated / chemistry*
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Hydrocarbons, Fluorinated / chemical synthesis
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Hydrocarbons, Fluorinated / chemistry*
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Molecular Structure
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Palladium / chemistry
Substances
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Aniline Compounds
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Benzophenones
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Carbamates
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Formic Acid Esters
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Hydrocarbons, Aromatic
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Hydrocarbons, Brominated
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Hydrocarbons, Fluorinated
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t-butyloxycarbonyl group
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Palladium
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benzophenone
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Ammonia