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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
Author(s) -
Guo Shenghai,
Wang Fang,
Sun Lincong,
Zhang Xinying,
Fan Xuesen
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800347
Subject(s) - chemistry , isoquinoline , annulation , catalysis , palladium , bond cleavage , carbonylation , isocyanate , medicinal chemistry , carbon monoxide , oxidative phosphorylation , combinatorial chemistry , stereochemistry , organic chemistry , polyurethane , biochemistry
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( sp 2 )−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.