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

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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 work-up 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.
Funding Information
  • Canada Foundation for Innovation (225006)
  • Fonds de Recherche du Qu?bec - Nature et Technologies (2014-RS-1711310)
  • Universit? de Montr?al
  • Natural Sciences and Engineering Research Council of Canada (RGPIN-2014-05281, CREATE 449307-2014)

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