Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalysts
In this work, some results of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone are presented. The employed catalysts were platinum-based modified with organotin precursors either chiral (Men3Sn-SnMen3) or achiral (SnBu4), and they were obtained via surface...
| Autores: | , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2005 |
| País: | Argentina |
| Institución: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/56075 |
| Acceso en línea: | http://hdl.handle.net/11336/56075 |
| Access Level: | acceso abierto |
| Palabra clave: | 3,4-Dimethoxyacetophenone Acetophenone Enantioselectivity Hydrogenation Men3sn-Snmen3 Organometallic Catalysts https://purl.org/becyt/ford/2.4 https://purl.org/becyt/ford/2 |
| Sumario: | In this work, some results of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone are presented. The employed catalysts were platinum-based modified with organotin precursors either chiral (Men3Sn-SnMen3) or achiral (SnBu4), and they were obtained via surface organometallic chemistry on metals (SOMC/M) techniques. The presence of organotin fragments on the catalyst surface inhibits the aromatic ring hydrogenation, leading to the hydrogenation of both acetophenone and 3,4-dimethoxyacetophenone to the corresponding alcohol with selectivity higher than 99%. With both substrates, a rate acceleration when changing from the achiral catalyst PtSn-OM to the chiral one, PtSn-OM* was observed. The presence of menthyl groups may be responsible for the rate acceleration in the key step of enantiodifferentiation. In the 3,4-dimethoxyacetophenone hydrogenation, 39% enantiomeric excess was obtained, with a selectivity of nearly 100%. |
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