Palladium-Catalyzed Alkenylation of Quinoline-N-oxides via C−H Activation under External-Oxidant-Free Conditions

The direct cross-coupling of quinoline-N-oxides with olefin derivatives has been realized using palladium acetate as the catalyst in the absence of external ligand and oxidant to give the corresponding 2-alkenylated quinolines and 1-alkenylated isoquinolines chemo- and regioselectively in 27−95% yie...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 131; no. 39; pp. 13888 - 13889
Main Authors Wu, Junliang, Cui, Xiuling, Chen, Lianmei, Jiang, Guojie, Wu, Yangjie
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.10.2009
Amer Chemical Soc
Subjects
Acrylates - chemistry
Alkenes - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclic N-Oxides - chemistry
Palladium - chemistry
Physical Sciences
Quinolines - chemistry
Science & Technology
HALIDES
DIRECT ARYLATION
AROMATIC KETONES
PYRIDINE
COUPLING REACTION
BOND ACTIVATION
MULTIPLE ARYLATION
REGIOSELECTIVE ARYLATION
HECK REACTION
ARYL CHLORIDES
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Summary:The direct cross-coupling of quinoline-N-oxides with olefin derivatives has been realized using palladium acetate as the catalyst in the absence of external ligand and oxidant to give the corresponding 2-alkenylated quinolines and 1-alkenylated isoquinolines chemo- and regioselectively in 27−95% yield. The catalytic process is proposed to proceed via direct C−H bond activation of the quinoline-N-oxide with Pd(OAc)2 followed by Heck coupling with the olefin. The resultant N-oxide of the alkenylated quinoline can oxidize the reduced Pd(0) to regenerate the Pd(II) active species and simultaneously release the 2-alkenylated quinoline without using any external oxidants and reductants.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja902762a