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Las reacciones de acoplamiento cruzado anidro heteroarilo-heteroarilo, Suzuki-Miyaura, habilitadas por el borato de

Vincent M Kassel¹, Christopher M Hanneman¹, Connor P Delaney¹

¹Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.

Journal of the American Chemical Society

|August 20, 2021

Resumen

Este estudio presenta un nuevo método para los acoplamientos cruzados Suzuki-Miyaura de compuestos heteroariles difíciles. Las condiciones optimizadas utilizan ésteres borónicos de neopentilo y trimetilsilanolato de potasio para reacciones eficientes.

Área de la Ciencia:

Química orgánica
Química sintética
Catálisis

Sus antecedentes:

El acoplamiento Suzuki-Miyaura es una reacción vital en la síntesis orgánica.
El acoplamiento de los compuestos heteroariles refractarios sigue siendo un desafío importante.
Los métodos existentes a menudo sufren de bajos rendimientos o condiciones adversas.

Objetivo del estudio:

Desarrollar condiciones de reacción eficientes para los acoplamientos cruzados de heteroarilo-heteroarilo Suzuki-Miyaura refractarios.
Para permitir el acoplamiento de una amplia gama de socios heteroariles ricos en π y deficientes en π.
Para lograr altos rendimientos en tiempos de reacción cortos.

Principales métodos:

Utilizó ésteres heteroarilborónicos de neopentilo como nucleófilos.
Utilizan bromuros y cloruros de heteroarilo como electrófilos.
Se utiliza trimetilsilanolato de potasio (TMSOK) como base soluble en condiciones anidras.
Se añade borato de trimetilo para aumentar las velocidades de reacción y prevenir el envenenamiento del catalizador.

Principales resultados:

Se han acoplado exitosamente diversos ésteres y haluros de boro heteroarilico.
Se obtienen buenos rendimientos para el desafío de los acoplamientos heteroarilo-heteroarilo.
Reacciones completas en tiempos de reacción cortos (3 horas o menos).

Conclusiones:

Desarrolló un método robusto para los acoplamientos cruzados Suzuki-Miyaura refractarios.
La adición de borato de trimetilo juega un papel crucial en la eficiencia de la reacción.
El método ofrece una herramienta versátil para sintetizar moléculas heteroaromáticas complejas.

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