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New Achievement in Catalytic Activation of C-H Bond of Imide Inner Salts
  English.dicp.cas.cn    Posted:2012-10-31

Recently, new progress in the activation of C-H bonds of imide inner salt molecules catalyzed over Rh(III) during the oxidation coupling reaction has been attained by the DICP research group 02T3 led by Prof. Xingwei Li, and the results were published as a short communication in the Angew. Chem., Intern. Ed. Of Germany (http://onlinelibrary.wiley.com/doi/10.1002/anie.201207204/abstract).

This DICP research team has realized multifunctional and unique C-H bond activation in imide inner salt substrates, as well as their subsequent oxidation coupling reaction with olefins. A series of important phenomena and results have been discovered:

1)   Under the action of the catalyst and silver oxidant, during the reaction of a series of benzaldehyde imide inner salts with olefins, the activation of the C-H bond and the breaking of the N-C single bond had occurred, with the final formation of six member ring 1,2-dihydrophthalazine products.

2)   Under similar conditions, during the reaction of imide inner salts of aromatic heterocyclic compounds (e.g., furan and pyrrole) with olefins, C-H bond activation and N-N single bond rupture had occurred, forming condensed-ring pyridine products. During this process, silver acted as an external oxidant, whilst the N-N bond in the reactants acted as an internal oxidant.

3)   In the presence of the catalyst and with Cu(II) as the oxidant, the reactions between imide inner salts of furan, pyrrole or indole and olefins gave rise to C-H bond activation and N=N double bond breaking (in-situ hydrolysis).

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