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Pd(0) / arilación intermolecular catalizada por PR3 de los enlaces C-H de sp3

Masayuki Wasa¹, Keary M Engle, Jin-Quan Yu

¹Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Journal of the American Chemical Society

|July 8, 2009

Resumen

La arilación C-H catalizada por paladio de ácidos carboxílicos alifáticos se logró utilizando ligandos de fosfina y yoduros de arilo. Este método permite la funcionalización de las moléculas de fármacos y la incorporación de flúor.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Química Medicinal La Química Medicinal es el campo de la Química Medicinal.

Sus antecedentes:

La funcionalización directa de los enlaces sp(3) C-H sigue siendo un desafío importante en la síntesis orgánica.
La catálisis de paladio ofrece potentes herramientas para la activación y la funcionalización de C-H.

Objetivo del estudio:

Desarrollar un nuevo protocolo de arilación intermolecular catalizada por el paladio para enlaces C-H sp{3}.
Para demostrar la utilidad de este método para modificar las moléculas de fármacos e introducir el flúor.

Principales métodos:

Se utilizó un sistema de catalizador de paladio (((0)) con ligandos de fosfina (PR ((3)).
Se emplean ioduros de arilo (ArI) como reactivos de arilación.
Aplicó el protocolo a varios derivados alifáticos del ácido carboxílico.

Principales resultados:

Se logró con éxito la arilación intermolecular de los enlaces sp(3) C-H en los derivados alifáticos del ácido carboxílico.
Demostró la aplicabilidad del método para funcionalizar moléculas de fármacos bioactivos.
Mostró la introducción del flúor utilizando yoduros de arilo fluorados.

Conclusiones:

Desarrolló un método eficiente Pd(0)-catalizado para la arylación C-H sp(3).
El protocolo proporciona una estrategia valiosa para la funcionalización en etapa tardía de moléculas complejas.
Permite la síntesis de nuevos compuestos fluorados con potenciales aplicaciones farmacéuticas.

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