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Oxidative Olefination of Secondary Amines with Carbon Nucleophiles
Author(s) -
Zhang YongGang,
Xu JingKun,
Li XiMing,
Tian ShiKai
Publication year - 2013
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.201300368
Subject(s) - chemistry , nucleophile , acetophenone , amine gas treating , malononitrile , benzoquinone , organic chemistry , stoichiometry , oxidative phosphorylation , imine , selectivity , medicinal chemistry , combinatorial chemistry , catalysis , biochemistry
An unprecedented olefination reaction of secondary amines with carbon nucleophiles has been developed through C–N/C–H functionalization under metal‐free oxidative conditions. In the presence of a stoichiometric amount of 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ), a range of secondary N ‐alkylanilines smoothly underwent oxidative olefination with 2‐alkylazaarenes, acetophenone, and malononitrile to give structurally diverse polysubstituted alkenes in moderate to excellent yields with excellent ( E ) selectivity. Preliminary mechanistic studies revealed that the oxidative olefination reaction proceeds through amine oxidation followed by imine olefination.