Cavitand based Polyphenols as Highly Reactive Organocatalysts for the Coupling of Carbon Dioxide and Oxiranes
Various cavitand based polyphenols were prepared from cheap and accessible aldehyde and resorcinol/pyrogallol reagents giving their respective resorcin[4]- or pyrogallol[4]arenes. The pre- organization of the phenolic units allows for intra- and intermolecular hydrogen bond (HB) networks affecting b...
| Autores: | , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2016 |
| País: | España |
| Institución: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repositorio: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:2072/356176 |
| Acceso en línea: | http://hdl.handle.net/2072/356176 https://doi.org/10.1002/cssc.201501463 |
| Access Level: | acceso abierto |
| Palabra clave: | 54 |
| Sumario: | Various cavitand based polyphenols were prepared from cheap and accessible aldehyde and resorcinol/pyrogallol reagents giving their respective resorcin[4]- or pyrogallol[4]arenes. The pre- organization of the phenolic units allows for intra- and intermolecular hydrogen bond (HB) networks affecting both the reactivity and stability of these HB donor catalysts. Unexpectedly, we found that resorcin[4]arenes show cooperative catalysis behavior compared to parent resorcinol in the catalytic coupling of epoxides and CO2 with significantly higher turnover. At elevated reaction temperatures, the resorcin[4]arene based catalyst 3d displays the best catalytic performance with both very high turnover numbers and frequencies combining increased reactivity and stability compared to pyrogallol, and ample substrate scope. This type of polyphenol structure thus illustrates the importance of a new, highly competitive organocatalyst design for devising sustainable CO2 conversion processes. |
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