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Hidroaminación intermolecular catalizada por iridio de alquenos alifáticos no activados con amidas y sulfonamidas
Christo S Sevov1, Jianrong Zhou, John F Hartwig
1Division of Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, California 94720, USA.
Journal of the American Chemical Society
|July 12, 2012
Resumen
Este estudio presenta un nuevo método catalítico para sintetizar N-alquilaminas mediante la adición de enlaces N-H a alquenos no activados. La reacción eficiente produce productos de aminas protegidas a partir de arylamidas y sulfonamidas.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis de la catálisis.
- Metodología sintética de la metodología sintética.
Sus antecedentes:
- La adición intermolecular de enlaces N-H a alquenos no activados es una estrategia sintética desafiante pero deseable.
- Las N-alquilaminas son bloques de construcción valiosos en la síntesis orgánica.
Objetivo del estudio:
- Desarrollar un método catalítico para la aminación intermolecular de alquenos no activados.
- Para sintetizar productos de aminas protegidas utilizando arylamidas y sulfonamidas.
Principales métodos:
- Reacción de aminación intermolecular catalítica. reacción de aminación intermolecular catalítica. reacciones de aminación intermoleculares. reacciones de aminación intermoleculares. reacciones de aminación intermoleculares. reacciones de aminación intermoleculares.
- Utilizó α-olefinas no activadas y bicicloalquenos como sustratos.
- Empleó arylamidas y sulfonamidas como donantes de bonos N-H.
Principales resultados:
- Alcanzó altos rendimientos de productos de aminas protegidas sintéticamente útiles.
- Demostró la aminación intermolecular de las α-olefinas y los bicicloalquenos no activados.
- Identificó un estado de reposo catalítico que involucra la adición oxidativa de enlaces N-H y la coordinación de amidas.
Conclusiones:
- Desarrolló un nuevo y eficiente método para la N-alquilación de alquenos.
- Elucidación de los pasos mecánicos clave, incluida la disociación de amidas y el reordenamiento intramolecular.
- Proporciona una valiosa ruta a las N-alquilaminas protegidas.
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