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Copper‐Catalyzed A3‐Coupling: Synthesis of 3‐Amino‐1,4‐diynes
Author(s) -
Choi YoonJeong,
Jang HyeYoung
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600343
Subject(s) - chemistry , alkyne , propargyl , catalysis , amine gas treating , aldehyde , coupling (piping) , coupling reaction , copper , combinatorial chemistry , medicinal chemistry , organic chemistry , mechanical engineering , engineering
Cu‐catalyzed A 3 (amine, aldehyde, and alkyne) coupling reactions were investigated for the synthesis of 3‐amino‐1,4‐diynes. Although metal‐catalyzed A 3 ‐coupling reactions have been extensively used to synthesize various propargylamines, the A 3 ‐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 A 3 ‐coupling. Unsymmetrical 3‐amino‐1,4‐diynes were also synthesized in 49–85 % yields by Cu‐catalyzed A 3 ‐coupling.
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