Abstract
Cu-catalyzed A3 (amine, aldehyde, and alkyne) coupling reactions were investigated for the synthesis of 3-amino-1,4-diynes. Although metal-catalyzed A3-coupling reactions have been extensively used to synthesize various propargylamines, the A3-coupling for the synthesis of 3-amino-1,4-diynes has been rarely reported. In this study, various symmetrical 3-amino-1,4-diynes were synthesized by the sequential Cu-catalyzed dealkynylation of propargyl aldehydes followed by A3-coupling. Unsymmetrical 3-amino-1,4-diynes were also synthesized in 49–85 % yields by Cu-catalyzed A3-coupling.
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