Magnetic superbasic proton sponges are readily removed and permit direct product isolation.

J Org Chem

Institute for Chemical and Bioengineering, Department of Chemistry and Applied Biosciences, ETH Zürich, Wolfgang-Pauli Strasse 10, CH-8093 Zurich, Switzerland.

Published: November 2014

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.

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Source
http://dx.doi.org/10.1021/jo501913zDOI Listing

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