期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 19, 页码 5658-5661出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201500864
关键词
carbocations; cycloaddition reactions; heterogeneous catalysis; propargyl alcohols; zeolites
资金
- Consolider-Ingenio
- Severo Ochoa program
- ITQ
The generation of a carbocation with an acid depends not only on the acid strength but also on the ability of the counteranion to stabilize the positive charge left behind. Here we report that despite their relatively weak acidity, zeolites are able to generate and stabilize medium-size (molecular weight approximate to 300 Da) delocalized carbocations on their surface under mild reaction conditions, as it can be done by strong Bronsted or Lewis acids in solution. The zeolite thus acts as a soft macroanion, prolonging the lifetime of the carbocation sufficiently to perform multifunctionalization reactions with amides, thioamides, and phenols, with high yield and selectivity. Biological studies show that some of the products obtained here present significant inhibition activity against colon cancer cells, illustrating the new possibilities of zeolites to prepare complex organic molecules.
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