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La carbonilación catalizada por el paladio de los tosilatos y mezilatos de arilo

Rachel H Munday¹, Joseph R Martinelli, Stephen L Buchwald

¹Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

Journal of the American Chemical Society

|February 9, 2008

Resumen

Un nuevo método de carbonilación catalizada por el paladio sintetiza de manera eficiente los ésteres de los tosilatos de arilo y los mesilatos en condiciones suaves. Este versátil protocolo demuestra un amplio alcance de sustrato y una excelente tolerancia de grupo funcional para la síntesis orgánica.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis es la catálisis.
Metodología sintética de la metodología sintética.

Sus antecedentes:

Las reacciones catalizadas por el paladio son cruciales en la síntesis orgánica moderna.
La síntesis eficiente de ésteres es vital para los productos farmacéuticos y los materiales.
Los tosilatos y mezilatos de arilo son productos intermedios sintéticos comunes.

Objetivo del estudio:

Desarrollar un protocolo general para la carbonilación catalizada por el paladio de los tosilatos y mesilatos de arilo.
Para sintetizar ésteres bajo condiciones suaves y eficientes.
Para demostrar el amplio alcance del sustrato y la tolerancia del grupo funcional.

Principales métodos:

Se utilizó un acetato de paladio (Pd(OAc) 2 y un sistema de catalizador de ligando dcpp.
Reacciones realizadas bajo presión atmosférica de monóxido de carbono (CO).
Operado a temperaturas entre 80 y 110 grados C.

Principales resultados:

Desarrolló con éxito un protocolo general para la síntesis de ésteres.
Se logra la carbonilación de sustratos ricos en electrones, pobres en electrones y heterocíclicos.
Se ha demostrado una amplia tolerancia del grupo funcional en el método desarrollado.

Conclusiones:

La carbonilación catalizada por el paladio desarrollada ofrece una ruta suave y eficiente a los ésteres.
El amplio alcance y la tolerancia del protocolo lo hacen valioso para diversas aplicaciones sintéticas.
Este método expande la utilidad de los tosilatos de arilo y los mesilatos en la síntesis orgánica.

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