Chemoselective Synthesis of Amines from Ammonium Hydroxide and Hydroxylamine in Continuous Flow

    • Clément Audubert
    • Alexanne Bouchard
    • Gary Mathieu
    • Hélène Lebel
    • Department of Chemistry and Centre in Green Chemistry and Catalysis (CGCC), Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, QC H3C 3J7, Canada

    The chemoselective amination of alkyl bromides and chlorides with aqueous ammonia and hydroxylamine was achieved in continuous flow to produce primary ammonium salts and hydroxylamines in high yields. An in-line workup was designed to isolate the corresponding primary amine, which was also telescoped in further reactions, such as acylation and Paal–Knorr pyrrole synthesis. Monosubstituted epoxides are also compatible with the reaction conditions.

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