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Intercambio de isótopos de carbono catalizado por paladio en cloruros de ácido alifático y benzoico

Donald R Gauthier¹, Nelo R Rivera¹, Haifeng Yang¹

¹Department of Process Research and Development , Merck & Co., Inc. , Rahway , New Jersey 07065 , United States.

Journal of the American Chemical Society

|November 3, 2018

Resumen

Un nuevo método catalizado por el paladio permite el intercambio simple de isótopos de carbono (carbono-13 y carbono-14) con compuestos de carbonilo. Esta técnica es útil para el etiquetado en etapa tardía de moléculas complejas como productos farmacéuticos y naturales.

Área de la Ciencia:

Química orgánica
Química de los isótopos
Catálisis

Sus antecedentes:

Los compuestos de carbonilo son intermedios sintéticos versátiles.
La incorporación de isótopos de carbono (por ejemplo, 13C, 14C) es crucial para los estudios mecanicistas, el seguimiento metabólico y el etiquetado radiactivo.
Los métodos existentes para el intercambio de isótopos de carbono pueden ser complejos o de alcance limitado.

Objetivo del estudio:

Desarrollar un protocolo operacionalmente simple para el intercambio de isótopos de carbono catalizados por paladio.
Demostrar la incorporación de 13CO y 14CO en los carbonilos alifáticos y benzoicos activados.
Mostrar la utilidad del método para la funcionalización en etapas tardías y su compatibilidad con diversos grupos funcionales.

Principales métodos:

Reacciones de carbonilación catalizadas por el paladio.
Uso de gas o sustitutos de 13CO y 14CO.
El ámbito de aplicación de los sustratos incluye los compuestos alifáticos y benzoicos de carbonilo activados.
Aplicación a los derivados de productos naturales y compuestos farmacéuticos.

Principales resultados:

Desarrollo exitoso de un protocolo simple para el intercambio de 13CO y 14CO.
Compatibilidad demostrada del grupo funcional con varios sustratos.
Preparación de varios componentes etiquetados con 13C y 14C, derivados de productos naturales y productos farmacéuticos.
El método permite la incorporación de isótopos de carbono en etapa tardía.

Conclusiones:

El protocolo presentado ofrece una vía eficiente y directa para la introducción de isótopos de carbono en moléculas orgánicas.
Este método es valioso para la síntesis de compuestos etiquetados para la investigación y el desarrollo, particularmente en la fase final de la funcionalidad.
La compatibilidad demostrada amplía la aplicabilidad del etiquetado por isótopos de carbono en la química medicinal y en la síntesis de productos naturales.

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