Directed CH Alkenylation of Quinoline N-Oxides at the C-8 Position Using a Cationic Rhodium(I) Catalyst

The cationic rhodium‐catalyzed alkenylation proceeds at the C‐8 position of quinoline N‐oxides. Regioselective CH bond activation was achieved by the directing effect of the anionic oxygen of an N‐oxide moiety, which can be readily removed by reductive treatment. A variety of 8‐alkenylated quinolin...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2014-05, Vol.356 (7), p.1516-1520
Main Authors: Shibata, Takanori, Matsuo, Yusuke
Format: Article
Language:English
Subjects:
Activation
alkenylation
Bonding
Catalysis
Catalysts
Cationic
Cations
CH activation
directing group
Hydrogen bonds
N-oxides
Oxides
Quinoline
Rhodium
rhodium catalysts
Synthesis
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Summary:The cationic rhodium‐catalyzed alkenylation proceeds at the C‐8 position of quinoline N‐oxides. Regioselective CH bond activation was achieved by the directing effect of the anionic oxygen of an N‐oxide moiety, which can be readily removed by reductive treatment. A variety of 8‐alkenylated quinoline N‐oxides was obtained in moderate to high yields.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201400223