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Arilación C-H catalizada por platino de arenos simples

Anna M Wagner¹, Amanda J Hickman, Melanie S Sanford

¹University of Michigan , Department of Chemistry, 930 North University Avenue, Ann Arbor, Michigan 48019, United States.

Journal of the American Chemical Society

|October 16, 2013

Resumen

El tetracloruro de platino de sodio (Na2PtCl4) cataliza la arilación C-H de las arenas. Los factores estéricos controlan la selectividad del sitio, con la arilación de naftaleno que muestra una selectividad opuesta en comparación con los catalizadores de paladio.

Área de la Ciencia:

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

Sus antecedentes:

La arilación C-H es una transformación crucial en la síntesis orgánica.
Las sales de diariliodonio son agentes arilados versátiles.
La catálisis de platino ofrece una reactividad alternativa al paladio.

Objetivo del estudio:

Para investigar el Na2PtCl4 como catalizador para la arilación C-H.
Para explorar la selectividad del sitio de la arylación catalizada por platino.
Para aclarar el mecanismo catalítico.

Principales métodos:

Arilación catalítica de C-H utilizando Na2PtCl4 y sales de diariliodonio.
Análisis de la selectividad del sitio en la funcionalización de arenas.
Estudios mecanicistas preliminares que incluyen análisis cinético.

Principales resultados:

Na2PtCl4 cataliza eficazmente la arilación C-H de las arenas.
La selectividad del sitio se rige principalmente por el obstáculo estérico.
La arilación de naftaleno con Na2PtCl4 muestra regioselectividad inversa en comparación con Na2PdCl4.4.
Los estudios mecánicos sugieren un ciclo Pt (II) / Pt (IV) con eliminación reductora que limita la velocidad.

Conclusiones:

Na2PtCl4 es un catalizador eficaz para la arilación C-H, ofreciendo perfiles de selectividad distintos.
El control estérico es un factor clave para dirigir la regioselectividad.
El ciclo catalítico involucra una pareja redox de platino, lo que lo diferencia de las vías catalizadas por paladio.

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