Divergent copper-catalyzed syntheses of 3-carboxylpyrroles and 3-cyanofurans from O -acetyl oximes and β-ketoesters/nitriles

The reaction between O -acetyl oximes and β-ketoesters/nitriles catalyzed by copper generated polysubstituted pyrroles and furans, respectively, under redox–neutral reaction conditions. Using this protocol, pyrroles or furans could be obtained simply by choosing an appropriate active methylene compo...

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Published inRSC advances Vol. 12; no. 41; pp. 26673 - 26679
Main Authors Almaraz-Ortiz, Wilfrido E., Ramos Orea, Aldahir, Casadiego-Díaz, Oscar, Reyes-Salgado, Agustín, Mejía-Galindo, Arturo, Torres-Ochoa, Rubén O.
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 16.09.2022
The Royal Society of Chemistry
Subjects
Chemistry
Copper
Furans
Nitriles
Oximes
Pyrroles
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Summary:The reaction between O -acetyl oximes and β-ketoesters/nitriles catalyzed by copper generated polysubstituted pyrroles and furans, respectively, under redox–neutral reaction conditions. Using this protocol, pyrroles or furans could be obtained simply by choosing an appropriate active methylene compound. Although both transformations occur essentially under the same reaction conditions, control experiments indicated that they follow different mechanistic pathways.
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These authors contributed equally to this work.
ISSN:2046-2069
2046-2069
DOI:10.1039/d2ra04938d