Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio-, and Site-Selective Three-Component Reaction with O -Acylhydroxylamines and Carboxylic Acids.
ACS catalysis(2019)
Abstract
A three-component reaction for 1,2-amino oxygenation of 1,3-dienes has been achieved using -acyl hydroxylamines and carboxylic acids. The reaction occurs through copper-catalyzed amination of olefins followed by nucleophilic addition of carboxylic acids, offering high levels of chemo-, regio-, and site-selectivity. The method is effective for both terminal and internal 1,3-dienes, including those bearing multiple, unsymmetrical substituents. The amino oxygenation conditions also exhibited remarkable selectivity toward 1,3-dienes over alkenes, good tolerance of sensitive functional groups, and reliable scalability.
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Key words
1,3-diene,amino oxygenation,copper catalysis
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