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Una reacción aeróbica invertida permite la síntesis selectiva de 1,3-dieno y 1,3,5-trieno a través de la escisión de

Neil J McAlpine¹, Long Wang¹, Brad P Carrow¹

¹Department of Chemistry , Princeton University , Princeton , New Jersey 08544 , United States.

Journal of the American Chemical Society

|October 6, 2018

Resumen

Los investigadores desarrollaron una nueva reacción aeróbica de boro Heck utilizando ciclobuteno para sintetizar eficientemente valiosos 1,3-dienos y 1,3,5-trienos lineales a partir de precursores simples. Este método ofrece un enfoque modular para estos importantes intermedios sintéticos.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Los 1,3-dienos sustituidos son bloques de construcción cruciales en la síntesis orgánica.
Los métodos existentes para preparar estos dienes a menudo son limitados en modularidad y simplicidad del precursor.
Las transformaciones catalíticas que involucran dienos están muy extendidas, pero requieren rutas sintéticas eficientes.

Objetivo del estudio:

Desarrollar un nuevo método catalítico modular para sintetizar 1,3-dienes sustituidos.
Para explorar el uso de ciclobuteno en una reacción de Heck de boro para la síntesis de dieno.
Investigar un enfoque aeróbico para una mayor sostenibilidad en la preparación de diene.

Principales métodos:

Reacción aeróbica de boro Heck utilizando ciclobuteno.
Utilizando ácidos (hetero) arilborónicos y ácidos alquenilborónicos como socios de acoplamiento.
Estudios experimentales y computacionales para elucidar el mecanismo de reacción.

Principales resultados:

Formación exclusiva de 1-arilo-1,3-dienos lineales a partir de ácidos arilborónicos.
Síntesis de 1,3,5-trienos a partir de ácidos alquenilborónicos.
Identificación de un mecanismo pericíclico que implica la escisión del enlace C-C en el ciclobuteno.

Conclusiones:

La reacción aeróbica de boro Heck desarrollada proporciona una ruta altamente modular y eficiente a valiosos compuestos de dieno y trieno.
La reacción elude las limitaciones de las reacciones tradicionales de tipo Heck al emplear un mecanismo único de escisión de enlaces pericíclicos C-C.
Esta metodología expande la utilidad sintética del ciclobuteno en las transformaciones catalíticas.

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