Palladium‐Catalyzed Oxidative Cyclocarbonylation of Isoquinolones with CO via C−H/N−H Bond Cleavage: Easy Access to Isoindolo[2,1‐b]isoquinoline‐5,7‐dione Derivatives

An efficient and practical synthesis of isoindolo[2,1‐b]isoquinoline‐5,7‐diones through Pd‐catalyzed C−H activation/carbonylative annulation of isoquinolones with CO (1 atm) is presented. Deuterium‐labeling experiments revealed that the aryl C(sp2)−H bond activation might be the rate‐determining ste...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-07, Vol.360 (13), p.2537-2545
Main Authors: Guo, Shenghai, Wang, Fang, Sun, Lincong, Zhang, Xinying, Fan, Xuesen
Format: Article
Language:English
Subjects:
Activation
Alkynes
Aromatic compounds
Carbon monoxide
Carbonyls
Cascade chemical reactions
Catalysis
Chemical reactions
Cyclocarbonylation
C−H activation
Deuterium
Diketones
Hydrogen bonds
Isoindolo[2,1-b]isoquinoline-5,7-dione
Isoquinolone
Organic chemistry
Palladium
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Summary:An efficient and practical synthesis of isoindolo[2,1‐b]isoquinoline‐5,7‐diones through Pd‐catalyzed C−H activation/carbonylative annulation of isoquinolones with CO (1 atm) is presented. Deuterium‐labeling experiments revealed that the aryl C(sp2)−H bond activation might be the rate‐determining step. More interestingly, the title compounds could also be prepared directly from the cascade reaction of N‐methoxy benzamides and internal alkynes, as the precursors of isoquinolones, under an atmospheric pressure of carbon monoxide through a Rh/Pd relay catalysis in a user‐friendly manner.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800347