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Acoplamiento oxidativo selectivo catalizado por Pd de anílidos con olefinas a través de la activación de enlaces C-H
Maarten D K Boele1, Gino P F van Strijdonck, André H M de Vries
1Institute of Molecular Chemistry, Faculty of Science, University of Amsterdam, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands.
Journal of the American Chemical Society
|February 21, 2002
Resumen
Los investigadores desarrollaron un nuevo método de activación de C-H catalizado por paladio para acoplar anílidos y acrilatos. Esta eficiente reacción a temperatura ambiente utiliza un oxidante de bajo costo y logra altos rendimientos.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis es la catálisis.
- Metodología sintética de la metodología sintética.
Sus antecedentes:
- La activación de C-H catalizada por paladio es una herramienta poderosa para la formación de enlaces C-C.
- Desarrollar métodos suaves y eficientes para la orto-funcionalización de anílidos sigue siendo un desafío.
Objetivo del estudio:
- Desarrollar una nueva reacción de acoplamiento oxidativo catalizada por el paladio entre derivados de anilido y acrilatos.
- Para lograr la activación del enlace C-H ortopédico en condiciones suaves.
Principales métodos:
- Se empleó la experimentación de alto rendimiento para examinar las condiciones de reacción.
- La reacción involucró catálisis de paladio, un ambiente ácido y benzoquinona como oxidante.
- Se analizaron estudios cinéticos y dependencia electrónica.
Principales resultados:
- Se descubrió una reacción selectiva y leve de acoplamiento oxidativo catalizado por paladio.
- La reacción procede a través de la activación de enlaces C-H orto de derivados de anilideo con acrilatos.
- Se lograron altos rendimientos (hasta el 91%) a temperatura ambiente utilizando benzoquinona como un oxidante rentable.
Conclusiones:
- El método desarrollado ofrece una ruta eficiente para sintetizar anilides funcionalizados.
- El mecanismo de reacción probablemente implica un ataque electrófilo por un complejo [PdOAc]+.
- La benzoquinona puede actuar como un ligando, estabilizando el catalizador de paladio.
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