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A 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 O(2), 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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Joe W. Wrigglesworth
Brian J. Cox
Guy C. Lloyd‐Jones
Organic Letters
University of Bristol
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Wrigglesworth et al. (Mon,) studied this question.
www.synapsesocial.com/papers/69fd9845015782f43c50c160 — DOI: https://doi.org/10.1021/ol202187h