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Las bis-hidrazonas C2-simétricas como ligandos en el acoplamiento cruzado asimétrico Suzuki-Miyaura

Antonio Bermejo¹, Abel Ros, Rosario Fernández

¹Departamento de Química Orgánica, Universidad de Sevilla, Apartado de Correos 1203, 41071 Seville, Spain.

Journal of the American Chemical Society

|November 5, 2008

Resumen

Un nuevo ligando de glyoxal bis-hidrazona permite acoplamientos cruzados asimétricos Suzuki-Miyaura sin fosfina. Este método produce eficientemente biarilos enriquecidos enantioméricamente a temperatura ambiente con alta selectividad.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Síntesis asimétrica de síntesis.

Sus antecedentes:

El acoplamiento cruzado Suzuki-Miyaura es una reacción vital para la formación de enlaces C-C.
El desarrollo de ligandos eficientes y selectivos es crucial para la catálisis asimétrica.
Los ligandos de fosfina se usan comúnmente, pero pueden ser tóxicos y sensibles al aire.

Objetivo del estudio:

Desarrollar un nuevo ligando libre de fosfina para el acoplamiento cruzado asimétrico Suzuki-Miyaura.
Para investigar la eficacia de un ligando de glyoxal bis-hidrazona derivado de (S,S)-1-amino-2,5-difenilpirrolidina.
Para lograr una alta enantioselectividad en la síntesis de compuestos biarílicos.

Principales métodos:

Síntesis del ligando glyoxal bis-hidrazona a partir de (S,S)-1-amino-2,5-difenilpirrolidina. también conocido como (S,S) -1-amino-2,5-difenilpirrolidina.
Preparación del complejo [PdCl2 ((bis-hidrazona)) ].
Aplicación del catalizador en reacciones asimétricas de acoplamiento cruzado Suzuki-Miyaura bajo condiciones suaves.

Principales resultados:

El ligando glyoxal bis-hidrazona demostró un excelente rendimiento en acoplamientos Suzuki-Miyaura sin fosfina.
El sistema catalítico proporcionó una variedad de biarilos enriquecidos enantioméricamente con diversos patrones de sustitución.
Las reacciones procedieron eficientemente a temperatura ambiente, dando como resultado productos con excelentes enantioselectividades.

Conclusiones:

La glyoxal bis-hidrazona es un ligando altamente efectivo para el acoplamiento cruzado asimétrico Suzuki-Miyaura.
Esta metodología ofrece una valiosa alternativa para la síntesis de enantiopuro biaryls.
El sistema catalítico desarrollado es activo, selectivo y opera bajo condiciones suaves.

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