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Palladium‐Catalyzed Aminomethylation of Nitrodienes and Dienones via Double C—N Bond Activation
Author(s) -
Yu Bangkui,
Gao Bao,
Zhang Xuexia,
Zhang Haocheng,
Huang Hanmin
Publication year - 2021
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000184
Subject(s) - chemistry , aminal , catalysis , palladium , alkyl , medicinal chemistry , double bond , combinatorial chemistry , stereochemistry , organic chemistry
Main observation and conclusion A new strategy for the generation of the active Pd‐alkyl species from aminal via C—N bond activation has been established, in which the formation of zwitterionic intermediate through aza‐Michael addition of aminal to nitrodienes or dienones is identified as a key step for the activation of the C—N bond. The efficient strategy has enabled a new palladium‐catalyzed α‐aminomethylation of nitrodienes and dienones via double C—N bond activation. The scope and versatility of the reaction were demonstrated and a broad range of substrates bearing electron‐donating and ‐withdrawing groups on the aromatic rings were all compatible with this reaction to furnish the desired α‐aminomethylated products in moderate to good yields with excellent regioselectivities and E / Z selectivities.