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Alquilación asimétrica de C-H a través del paladio ((II) / cis-ArSOX
Wei Liu1, Siraj Z Ali1, Stephen E Ammann1
1Roger Adams Laboratory, Department of Chemistry , University of Illinois , Urbana , Illinois 61801 , United States.
Journal of the American Chemical Society
|August 10, 2018
Resumen
Los investigadores desarrollaron nuevos catalizadores de paladio (Pd) / cis-arilo sulfóxido-oxazolina) para la alquilación asimétrica de C-H. Estos catalizadores demuestran un amplio alcance y una alta enantioselectividad en reacciones con varios nucleófilos.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Síntesis asimétrica
Sus antecedentes:
- La alquilación C-H es una transformación crucial en la síntesis orgánica.
- El desarrollo de catalizadores eficientes y selectivos para la funcionalización asimétrica C-H sigue siendo un desafío importante.
Objetivo del estudio:
- Informar sobre el desarrollo de nuevos catalizadores de paladio (II) con ligandos cis-arilo sulfóxido-oxazolina (cis-ArSOX).
- Explorar la aplicación de estos catalizadores en la alquilación asimétrica C-H de las olefinas terminales.
Principales métodos:
- Síntesis de ligandos cis-ArSOX modulares y sintonizables.
- Reacciones catalíticas asimétricas de alquilación de C-H utilizando sistemas Pd (II) /cis-ArSOX.
- Evaluación del alcance de la reacción, la enantioselectividad y la diastereoselectividad.
Principales resultados:
- Se logró un amplio alcance sin precedentes y una alta enantioselectividad (promedio > 90% ee) en 37 ejemplos.
- Se ha demostrado una alta reactividad y una diastereoselectividad controlada por catalizadores en la alquilación de olefinas alifáticas.
- La estabilidad oxidativa del andamio ArSOX fue crucial para el rendimiento del catalizador.
Conclusiones:
- Los catalizadores desarrollados Pd (II) /cis-ArSOX representan un avance significativo en la alquilación asimétrica de C-H.
- Esta nueva clase de ligandos quirales es prometedora para otros procesos de transición oxidativa catalizados por metales.
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