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Carbonylation Access to Phthalimides Using Self-Sufficient Directing Group and Nucleophile

Fanghua Ji, Jianxiao Li, Xianwei Li , Wei Guo, Wanqing Wu* and Huanfeng Jiang*

*School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China, Email: cewuwqscut.edu.cn, jianghfscut.edu.cn

F. Ji, J. Li, X. Li, W. Guo, W. Wu, H. Jiang, J. Org. Chem., 2018, 83, 104-112.

DOI: 10.1021/acs.joc.7b02433 (free Supporting Information)


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Abstract

In a palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides, an imine and H2O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily available materials with high atom- and step-economy in a one-pot manner.

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proposed mechanism



Key Words

phthalimides, copper(II) oxide, oxygen


ID: J42-Y2018