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Chemoselective Synthesis of Amines from Ammonium Hydroxide and Hydroxylamine in Continuous Flow
Clément Audubert1, Alexanne Bouchard1, Gary Mathieu1
1Department of Chemistry and Centre in Green Chemistry and Catalysis (CGCC) , Université de Montréal , P.O. Box 6128, Station Downtown , Montréal , QC H3C 3J7 , Canada.
Abstract:
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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