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New heteroannulation reactions of n-alkoxybenzamides by Pd(II) catalyzed C–H activation
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posted on 2023-06-08, 19:29 authored by Joe W Wrigglesworth, Brian Cox, Guy C Lloyd-Jones, Kevin I Booker-MilburnA new palladium(II) catalyzed methodology for the direct synthesis of alkylidene isoindolinones from N-alkoxybenzamides is presented. Isoindolinone formation proceeds through a highly efficient and E-selective C–H activation/Heck/Aza-Wacker sequence. Substoichiometric amounts of benzoquinone can be employed in a cooperative oxidation system with O2, leading to facile purification of products. Modification of the reaction conditions provides a general route to substituted phthalimides by carbonylation with CO. Both systems were found to tolerate a wide range of functionality.
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Publication status
- Published
Journal
Organic LettersISSN
1523-7060Publisher
American Chemical SocietyExternal DOI
Issue
19Volume
13Page range
5326-5329Department affiliated with
- Chemistry Publications
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- No
Peer reviewed?
- Yes
Legacy Posted Date
2015-01-12Usage metrics
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