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Aminación oxidativa aeróbica de alquenos no activados catalizados por el paladio
Jodie L Brice1, Jenna E Harang, Vitaliy I Timokhin
1Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.
Journal of the American Chemical Society
|March 3, 2005
Resumen
Los investigadores desarrollaron la primera aminación oxidativa catalizada por el paladio para olefinas de alquilo no activadas. Estas reacciones no requieren un cocatalizador y utilizan la rotación directa del catalizador de paladio acoplado al dioxígeno, lo que sugiere un mecanismo de cis-aminopaladación.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis de la catálisis.
Sus antecedentes:
- Las reacciones catalizadas por el paladio son cruciales en la síntesis orgánica.
- La aminación oxidativa de las olefinas es una transformación valiosa para crear enlaces C-N.
- Las olefinas de alquilo no activadas presentan un desafío sintético significativo.
Objetivo del estudio:
- Para informar de la primera aminación oxidativa catalizada por el paladio exitosa de las olefinas de alquilo no activadas.
- Establecer las condiciones para la rotación directa de catalizadores acoplados al dioxígeno sin cocatalizadores.
Principales métodos:
- Utilizó la catálisis del paladio para la aminación oxidativa.
- Empleado el dioxígeno directo como el oxidante.
- Reacciones investigadas utilizando norboreno y otros alquenos cíclicos.
- Reacciones realizadas en condiciones libres de cocatalizadores.
Principales resultados:
- Logró los primeros ejemplos de aminación oxidativa catalizada por el paladio de olefinas de alquilo no activadas.
- Demostrado éxito en la rotación del catalizador utilizando dioxígeno directo.
- Productos de reacción identificados consistentes con un mecanismo de cis-aminopaladación.
Conclusiones:
- La catálisis de paladio acoplado a dioxígeno y libre de cocatalista permite la aminación oxidativa de sustratos difíciles.
- Los productos observados apoyan una vía de cis-aminopaladación en estas nuevas reacciones.
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