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Cu‐Catalyzed Selective Synthesis of Propargylamines via A 3 ‐Coupling/ Aza ‐Michael Addition Sequence: Amine Loading Controls the Selectivity
Author(s) -
Feng Huangdi,
Peng Futao,
Xi Hui,
Zhong Ling,
Huang Liliang
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100079
Subject(s) - chemistry , michael reaction , alkyne , selectivity , amine gas treating , catalysis , combinatorial chemistry , mannich reaction , olefin fiber , coupling reaction , organic chemistry
Propargylamines are valuable molecules in medicinal chemistry and organic synthesis. A 3 reaction is straightforward access to construct propargylamine and its derivatives. Here we report operationally simple catalytic domino A 3 ‐coupling/ aza ‐Michael addition of a primary amine, formaldehyde solution, an alkyne, and an olefin using copper as a catalyst to produce a series of functionalized propargylamines in moderate to excellent yields. This protocol involves a competition between aza ‐Michael addition and Mannich reaction. By changing the amount loading of amines to control the process of Mannich reaction is the key procedure of increasing the selectivity.