Sonsona, Isaac G. and Marques-Lopez, Eugenia and Haering, Marleen and Diaz, David Diaz and Herrera, Raquel P. (2018) Urea Activation by an External Bronsted Acid: Breaking Self-Association and Tuning Catalytic Performance. CATALYSTS, 8 (8): 305. ISSN 2073-4344,
Full text not available from this repository. (Request a copy)Abstract
In this work, we hypothesize that Bronsted acids can activate urea-based catalysts by diminishing its self-assembly tendency. As a proof of concept, we used the asymmetric Friedel-Crafts alkylation of indoles with nitroalkenes as a benchmark reaction. The resulting 3-substituted indole derivatives were obtained with better results due to cooperative effects of the chiral urea and a Bronsted acid additive. Such synergy has been rationalized in terms of disassembly of the supramolecular catalyst aggregates, affording a more acidic and rigid catalytic complex.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | FRIEDEL-CRAFTS ALKYLATION; HYDROGEN-BONDING NETWORKS; AZA-HENRY REACTION; ASYMMETRIC ORGANOCATALYSIS; BIFUNCTIONAL ORGANOCATALYSTS; THIOUREA ORGANOCATALYSTS; MOLECULAR RECOGNITION; SUPRAMOLECULAR GELS; NMR-SPECTROSCOPY; INDOLES; Bronsted acids; Friedel-Crafts; organocatalysis; self-association; synergy; urea |
| 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: | 11 Mar 2020 12:42 |
| Last Modified: | 11 Mar 2020 12:42 |
| URI: | https://pred.uni-regensburg.de/id/eprint/14098 |
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