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Acoplamiento catalítico de alcoholes secundarios

Subramanian Thiyagarajan¹, Chidambaram Gunanathan¹

¹School of Chemical Sciences , National Institute of Science Education and Research , HBNI, Bhubaneswar - 752050 , India.

Journal of the American Chemical Society

|February 22, 2019

Resumen

Este estudio introduce un nuevo acoplamiento catalizado por rutenio de alcoholes secundarios, sintetizando eficientemente diversas cetonas β-disubstituidas. El enfoque de la química verde utiliza un único catalizador para la formación selectiva de enlaces C-C con agua e hidrógeno como subproductos.

Área de la Ciencia:

Química orgánica
Catálisis
Química ecológica

Sus antecedentes:

El acoplamiento directo de alcohol es un reto.
La síntesis selectiva de cetonas es crucial.

Objetivo del estudio:

Desarrollar un nuevo método catalítico para el acoplamiento directo de alcoholes secundarios.
Sintetiza cetonas β-disubstituidas con una alta selectividad.

Principales métodos:

El rutenio (II) catalizó la reacción de acoplamiento cruzado directo.
Utilizado catalizador Ru-MACHO con cooperación amina-amida y ligando metálico.
El alcance del sustrato investigado incluye alcoholes cíclicos, acíclicos, simétricos y no simétricos.

Principales resultados:

Se logra el acoplamiento cruzado selectivo de dos alcoholes secundarios diferentes para formar cetonas β-disubstituidas.
Se ha demostrado un amplio alcance de sustrato con varios tipos de alcohol.
Diastereoselectividad inducida por el producto y efectos de impedimento estérico observados.
Se identificó una oxidación más rápida de los alcoholes alifáticos sobre los bencílicos a través de estudios cinéticos.

Conclusiones:

Estableció una metodología de formación de enlaces C-C sin precedentes, más ecológica y atómica.
El protocolo requiere una carga de catalizador baja y una base catalítica.
Producido sólo H2 y H2O como subproductos, destacando sus beneficios ambientales.

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