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  • Magnetic Superbasic Proton ...
    Schneider, Elia M; Raso, Renzo A; Hofer, Corinne J; Zeltner, Martin; Stettler, Robert D; Hess, Samuel C; Grass, Robert N; Stark, Wendelin J

    Journal of organic chemistry, 11/2014, Letnik: 79, Številka: 22
    Journal Article

    Workup in organic synthesis can be very time-consuming, particularly when using reagents with both a solubility similar to that of the desired products and a tendency not to crystallize. In this respect, reactions involving organic bases would strongly benefit from a tremendously simplified separation process. Therefore, we synthesized a derivative of the superbasic proton sponge 1,8-bis(dimethylamino)naphthalene (DMAN) and covalently linked it to the strongest currently available nanomagnets based on carbon-coated cobalt metal nanoparticles. The immobilized magnetic superbase reagent was tested in Knoevenagel- and Claisen–Schmidt-type condensations and showed conversions of up to 99%. High yields of up to 97% isolated product could be obtained by simple recrystallization without using column chromatography. Recycling the catalyst was simple and fast with an insignificant decrease in catalytic activity.