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Acoplamiento oxidativo catalizado por oro de arilsilanos y arenos: origen de la selectividad y mejora del

Liam T Ball¹, Guy C Lloyd-Jones, Christopher A Russell

¹School of Chemistry, University of Edinburgh , Joseph Black Building, West Mains Road, Edinburgh EH9 3JJ, U.K.

Journal of the American Chemical Society

|December 26, 2013

Resumen

La catálisis del oro permite el acoplamiento selectivo de arenos con silanos a través de un ciclo redox Au (I) / Au (III). Este mecanismo explica la alta selectividad en las reacciones de heteroacoplamiento, cruciales para la química sintética.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
La catálisis es la catálisis.
Química orgánica sintética y orgánica.

Sus antecedentes:

La catálisis del oro es una herramienta poderosa para la formación de enlaces C-C.
Comprender los mecanismos de reacción es clave para optimizar los procesos catalíticos.

Objetivo del estudio:

Para dilucidar el mecanismo de acoplamiento catalizado por oro entre arenas y ariltrimetilsilanos.
Para investigar el origen de la selectividad en estas reacciones de acoplamiento.

Principales métodos:

Análisis cinético utilizando un precatalizador mejorado (thtAuBr3).
Relaciones lineales de energía libre.
Efectos del isótopo cinético. efectos del isótopo cinético.
Experimentos estoiquiométricos. experimentaciones estoiquiométricas. experimentaciones estoiquiométricas. experimentaciones estoiquiométricas. experimentos estoiquiométricos.

Principales resultados:

La reacción se lleva a cabo a través de un ciclo redox Au (I) / Au (III).
Sustitución aromática electrofílica secuencial por Au (III) en el arilsilano y el areno.
Eliminación reductora y reoxidación del oro formando productos.
Alta selectividad para el heteroacoplamiento sobre el homoacoplamiento.
El paso de limitación de la facturación implica la sustitución asociativa de un complejo π de arenas.

Conclusiones:

El mecanismo propuesto describe con precisión el acoplamiento catalizado por oro.
Las diferencias en los pasos de determinación del producto explican la quimioselectividad observada.
Las ideas sobre la etapa de limitación de la tasa informan la implementación de la metodología.

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