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Highly efficient catalysis of retro-claisen reactions: From a quinone derivative to functionalized imidazolium salts

AuthorsVisbal, Renso ; Laguna, Antonio ; Gimeno, M. Concepción
KeywordsNitrogen heterocycles
Retro-Claisen reaction
Synthetic methods
C−C activation
Issue Date2016
CitationChemistry - A European Journal 22(12): 4189-4195 (2016)
AbstractA new and efficient method for the preparation of several imidazolium salts containing an ester group in the C4 position of the aromatic ring through a retro-Claisen reaction pathway between a quinone derivative and several alcohols is described. This new organic transformation proceeds in the absence of a catalyst, but it is greatly catalyzed by different Lewis acids, especially with AgOAc at a very low catalyst loading and in very short reaction times. The process takes place by the nucleophilic attack of the carbonyl groups by the alcohol functionality, thus promoting a double C-C bond cleavage and C-H and C-O bond formation. This reaction represents the first example of this type between a quinone derivative and alcohols.
Identifiersdoi: 10.1002/chem.201505095
e-issn: 1521-3765
issn: 0947-6539
Appears in Collections:(ISQCH) Artículos
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