Urea activation by an external brønsted acid: Breaking self-association and tuning catalytic performance
In this work, we hypothesize that Brønsted 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 w...
| Autores: | , , , , |
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| Tipo de documento: | artigo |
| Estado: | Versão publicada |
| Data de publicação: | 2018 |
| País: | España |
| Recursos: | Universidad de Zaragoza |
| Repositório: | Zaguán. Repositorio Digital de la Universidad de Zaragoza |
| OAI Identifier: | oai:zaguan.unizar.es:74967 |
| Acesso em linha: | http://zaguan.unizar.es/record/74967 |
| Access Level: | Acceso aberto |
| Resumo: | In this work, we hypothesize that Brønsted 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 Brønsted acid additive. Such synergy has been rationalized in terms of disassembly of the supramolecular catalyst aggregates, affording a more acidic and rigid catalytic complex. |
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