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Acoplamiento cruzado habilitado por ligandos de enlaces C(sp(3)) -H con arilsilanes

Jian He¹, Ryosuke Takise¹, Haiyan Fu¹

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

Journal of the American Chemical Society

|March 31, 2015

Resumen

Este estudio introduce el primer acoplamiento cruzado catalizado por el paladio de enlaces C(sp(3)) -H con compuestos organosilicones. Un nuevo ligando a base de quinolina demostró ser esencial para este avance significativo en la síntesis orgánica.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Química organometálica Química orgánica de los metales.

Sus antecedentes:

Las reacciones de acoplamiento cruzado catalizadas por paladio son fundamentales en la síntesis orgánica.
La activación de los bonos C(sp(3)) -H sigue siendo un desafío importante.
Los compuestos orgánicos de silicio son socios de acoplamiento versátiles.

Objetivo del estudio:

Desarrollar un nuevo método para el acoplamiento cruzado catalizado por paladio de enlaces C (((sp ((3)) -H.
Para utilizar compuestos organosilicon como socios de acoplamiento en la funcionalización C (((sp (((3)) -H.
Para identificar los ligandos clave que permiten estas transformaciones desafiantes.

Principales métodos:

Se empleó la catálisis de paládio (II).
Se utilizó un ligando a base de quinolina recientemente desarrollado.
Las reacciones involucraron el acoplamiento cruzado de enlaces C(sp(3)) -H con reactivos de organosilicio.

Principales resultados:

Logró el primer acoplamiento cruzado catalizado por paladio exitoso de enlaces C (((sp (((3)) -H con socios de acoplamiento de organosilicio.
Demostró el papel crucial del nuevo ligando a base de quinolina en la facilitación de la reacción.
Se estableció una nueva ruta sintética para la funcionalización C (((sp(3)) -H.

Conclusiones:

El desarrollo de un nuevo ligando a base de quinolina es clave para permitir el acoplamiento cruzado Pd{II}-catalizado C{sp}3)) -H/organosilicon.
Este trabajo amplía el alcance de las metodologías de activación de C-H y acoplamiento cruzado.
Ofrece una nueva estrategia para la síntesis de moléculas orgánicas complejas.

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