Preparation, Characterization, and Synthetic Uses of Lanthanide(III) Catalysts Supported on Ion Exchange Resins

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Abstract

Lanthanide(III) catalysts supported on ion exchange resins (Ln-resins) were prepared from Dowex, Amberlite, Amberlyst, and other cation exchange resins. The amount of lanthanides on resin supports was measured through EDTA titration. The results indicated that the lanthanides in aqueous solution exchanged with almost all the cations (H+ or Na+) on the resins to form stable ionic complexes between the lanthanides(III) and the resins. The effects of resin types, resin sizes, and lanthanide salts were investigated with a reaction of indole and hexanal in aqueous solution and with an aldol reaction of benzaldehyde and silyl enol ether in organic solvents. The study found that among ion exchange resins tested Amberlyst XN-1010 and Amberlyst 15 complexed with lanthanides(III) were the most effective catalysts. In addition, the selective Ln-resins were utilized to catalyze acetalization of aldehydes, aldol reaction of formaldehyde or benzaldehyde in aqueous solution, nucleophilic addition to an imine, allylation of an aldehyde, an aza Diels−Alder (DA) reaction, and a ring-opening reaction of an epoxide. Furthermore, glycosylation of alcohol using glucosyl fluoride as a donor was also promoted with the Ln-resin. Thus, this work demonstrated potential uses of lanthanide(III) catalysts supported on ion exchange resins in routine organic reactions.

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