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Palladium‐Catalyzed Cascade Double C—N Bond Activation: A New Strategy for Aminomethylation of 1,3‐Dienes with Aminals
Author(s) -
Qiao Cuifang,
Chen Anrong,
Gao Bingjian,
Liu Yang,
Huang Hanmin
Publication year - 2018
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.201800205
Subject(s) - chemistry , allylic rearrangement , palladium , catalysis , regioselectivity , aminal , double bond , medicinal chemistry , polymer chemistry , combinatorial chemistry , organic chemistry
A new palladium‐catalyzed selective aminomethylation of conjugated 1,3‐dienes with aminals via double C—N bond activation is described. This simple method provides an effective and rapid approach for the synthesis of linear α,β‐unsaturated allylic amines with perfect regioselectivity. Mechanistic studies disclosed that one palladium catalyst cleaved two distinct C—N bond to furnish a cascade double C—N bond activation, in which an allylic 1,3‐diamine and allylic 1,2‐diamine were initially formed as key intermediates through the palladium‐catalyzed C—N bond activation of aminal and the α,β‐unsaturated allylic amine was subsequently produced via palladium‐catalyzed C—N bond activation of the allylic diamines.