Nitrilimine cycloadditions catalyzed by iron oxide nanoparticles
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Nitrilimine cycloadditions to ethylenes, acetylenes, and activated nitriles have been exploited in the presence of catalytic amounts of oleic-acid-coated iron oxide nanoparticles (diameter = 11.9 ± 1.0 nm). The reactions were fully regioselective with monosubstituted ethylenes and ethyl cyanoformiate, while mixtures of cycloadducts were obtained in the presence of methyl propiolate. The intervention of iron oxide nanoparticles allowed carrying out the cycloadditions at milder conditions compared to the metal-free thermal processes. A labile intermediate has been proposed to explain this behavior.
KeywordsDipolar cycloadditions Nitrilimines Catalysis Magnetic nanoparticles Nanoparticle catalysis
The authors are grateful to F. Cargnoni (ISTM-CNR, Milan) for useful suggestions about the DFT calculations.
G.M. and A.P. together conceived and planned the research, discussed the results, and wrote the manuscript. G.M. carried out all the cycloadditions. A.M.F. and S.M. synthesized the nanoparticles and A.M.F. characterized them. A.P. carried out the calculations. All the authors read and approved the final manuscript.
Compliance with ethical standards
Conflict of interest
The authors declare that they have no conflict of interest.
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