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![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
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Reacción endoselectiva de sililmetilheck catalizada por Pd en la reacción de Heck
Marvin Parasram1, Viktor O Iaroshenko, Vladimir Gevorgyan
1Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.
Journal of the American Chemical Society
|December 16, 2014
Resumen
Una nueva reacción de Heck catalizada por el paladio que utiliza éteres silílicos permite la síntesis de compuestos cíclicos. Este proceso asistido por silicio logra una alta endo selectividad y produce valiosos (Z) -alquenildiolos.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis de la catálisis.
- Metodología sintética de la metodología sintética.
Sus antecedentes:
- La reacción de Heck es una herramienta poderosa para la formación de enlaces carbono-carbono.
- Lograr una alta estereoselectividad en las reacciones de Heck sigue siendo un desafío.
- Los reactivos que contienen silicio ofrecen perfiles únicos de reactividad y selectividad.
Objetivo del estudio:
- Desarrollar una nueva reacción de Heck catalizada por paladio para la síntesis de compuestos cíclicos.
- Investigar el mecanismo y el resultado estereoquímico de esta nueva reacción.
- Explorar la utilidad de los productos sintetizados.
Principales métodos:
- Reacción de Heck catalizada por paladio utilizando éteres yodometilsililo de fenoles y alquenolos alifáticos.
- Estudios mecanicistas que involucran vías híbridas de radicales de paladio.
- La oxidación de los sililociciclos alilicos a los (Z) -alquenildiolos.
Principales resultados:
- Desarrollo de una reacción de Heck endo-selectiva.
- Identificación de un mecanismo híbrido de radicales de paladio y radicales de paladio.
- Demostrando el papel crucial del silicio en el logro de la endo selectividad.
- Síntesis exitosa de (Z) -alquenildiolos a partir de los productos de reacción.
Conclusiones:
- Se ha establecido una nueva y eficiente reacción silil metil Heck.
- La reacción se produce a través de un mecanismo híbrido único de radicales de paladio y radicales de paladio.
- El silicio juega un papel clave en el control de la endo selectividad.
- La metodología desarrollada proporciona acceso a valiosos (Z) -alquenildiolos.
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