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Un nuevo paradigma para la formación de enlaces carbono-carbono: acoplamiento cruzado aeróbico con plantilla de cobre

Janette M Villalobos¹, Jiri Srogl, Lanny S Liebeskind

¹Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.

Journal of the American Chemical Society

|December 1, 2007

Resumen

La catálisis del cobre permite la síntesis de cetonas a partir de ésteres de tiol y ácidos borónicos. Esta reacción aeróbica procede de manera eficiente a temperaturas suaves y pH neutro, ofreciendo una nueva ruta para la formación de enlaces carbono-carbono.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Metodología sintética de la metodología sintética.

Sus antecedentes:

Los ésteres de tiol y los ácidos borónicos son compuestos orgánicos versátiles.
Los métodos eficientes para la síntesis de cetonas son cruciales en la química orgánica.
Las reacciones catalizadas por el cobre ofrecen una reactividad y una selectividad únicas.

Objetivo del estudio:

Desarrollar un nuevo método catalítico para la síntesis de cetonas.
Para explorar la reacción entre los ésteres de tiol y los ácidos borónicos.
Para investigar la formación de enlaces carbono-carbono mediados por el cobre.

Principales métodos:

Utilizando cantidades catalíticas de sales de Cobre (I) o de Cobre (II).
Empleando ésteres de tiol derivados de las voluminosas 2-amidas de tiosalicilamidas.
Llevar a cabo la reacción en condiciones aeróbicas a pH neutro y temperaturas suaves (temperatura ambiente a 50°C).

Principales resultados:

La formación de cetonas se logró a partir de ésteres de tiol y ácidos borónicos.
La reacción procedió eficientemente en condiciones aeróbicas con cobre catalítico.
El uso de derivados voluminosos de tiosalicilamida facilitó la reacción.
Se propuso una vía mecánicamente sin precedentes que involucra el templado de cobre.

Conclusiones:

Se ha establecido una nueva síntesis aeróbica catalizada por cobre de cetonas a partir de ésteres de tiol y ácidos borónicos.
Este método proporciona una ruta eficiente para la formación de enlaces C-C en condiciones suaves.
El sistema catalítico es efectivo utilizando sales de cobre fácilmente disponibles y sustratos específicos de ésteres de tiol.

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