Kuehbeck, Dennis and Mayr, Judith and Haering, Marleen and Hofmann, Martin and Quignard, Francoise and Diaz Diaz, David (2015) Evaluation of the nitroaldol reaction in the presence of metal ion-crosslinked alginates. NEW JOURNAL OF CHEMISTRY, 39 (3). pp. 2306-2315. ISSN 1144-0546, 1369-9261
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Understanding the ability of biopolymers to promote selective C-C bond formation could provide important insights into the molecular mechanisms underlying evolution, and could help in the design of safer and "greener'' catalysts in the future. This work describes the preparation of metal ion-crosslinked alginate materials and the evaluation of their potential catalytic activity towards the Henry (nitroaldol) reaction between a variety of aldehydes and nitroalkanes. The results demonstrated broad substrate specificity and a remarkable influence of the solvent nature, metal ion, and physical state of the alginate-based catalysts. In this sense, Ca2+-alginate hydrogel beads in DMSO used as a heterogeneous and recyclable catalyst were found to be the most efficient system, although the reaction could also proceed in an aqueous medium. Moreover, both small and large-scale model reactions between 4-nitrobenzaldehyde and nitromethane were performed successfully at room temperature. The possibility of coupling the reaction with an enzymatic resolution of the so-obtained beta-nitroalcohol products was also assessed. All materials were characterized using different techniques including, among others, FT-IR, TGA, ICP-OES, and FE-SEM.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | C BOND FORMATION; ENANTIOSELECTIVE HENRY REACTIONS; HIGH CATALYTIC-ACTIVITY; EGG-BOX MODEL; CALCIUM; NANOPARTICLES; LIPASES; BEADS; GELS; 4-NITROPHENOL; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. David Díaz Díaz |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 31 Jul 2019 09:01 |
| Last Modified: | 31 Jul 2019 09:01 |
| URI: | https://pred.uni-regensburg.de/id/eprint/6252 |
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