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Transmisión de un solo electrón: una tecnología habilitadora para el acoplamiento cruzado secundario de alquilborón
David N Primer1, Idris Karakaya, John C Tellis
1Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.
Journal of the American Chemical Society
|February 5, 2015
Resumen
Un nuevo mecanismo de transferencia de un solo electrón permite reacciones de acoplamiento cruzado suaves. Este método une de manera eficiente los grupos alquilo secundarios a los haluros de arilo utilizando catalizadores de iridio y níquel.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis es la catálisis.
- Metodología sintética de la metodología sintética.
Sus antecedentes:
- La transmetalización es crucial para las reacciones de acoplamiento cruzado.
- Los métodos tradicionales a menudo requieren condiciones duras o sustratos específicos.
- El desarrollo de protocolos de acoplamiento cruzado más suaves y generales es un desafío continuo.
Objetivo del estudio:
- Introducir un nuevo mecanismo de transferencia de alquilo mediado por un solo electrón.
- Establecer las condiciones generales para el acoplamiento cruzado de grupos alquilo secundarios con haluros de arilo.
- Para demostrar la utilidad de la fotorreducción y la catálisis del níquel en esta transformación.
Principales métodos:
- Utilizando un catalizador de fotorredóxido de iridio en conjunto con un catalizador de acoplamiento cruzado de níquel.
- El uso de alquiltrifluoroboratos secundarios como agentes de alquilación.
- Reaccionando con una amplia gama de bromuros de arilo bajo condiciones suaves.
Principales resultados:
- Acoplamiento cruzado exitoso de alquiltrifluoroboratos secundarios con varios bromuros de arilo.
- Demostración de una nueva vía de transferencia de un solo electrón para la transmesación.
- Se logra el acoplamiento cruzado en condiciones suaves, ampliamente aplicables.
Conclusiones:
- La transferencia de alquilo mediada por un solo electrón proporciona una nueva ruta eficiente para el acoplamiento cruzado.
- El método desarrollado ofrece un enfoque suave y general para la formación de enlaces C ((sp3) -C ((sp2).
- Este trabajo amplía el alcance de las reacciones de acoplamiento cruzado catalítico.
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