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Hidroboración selectiva de N-heteroarenos catalizados por el hierro

Fanjun Zhang¹, Heng Song¹, Xuewen Zhuang¹

¹School of Chemistry and Chemical Engineering, Shandong University , No. 27 South Shanda Road, Jinan 250100, China.

Journal of the American Chemical Society

|December 2, 2017

Resumen

Un nuevo complejo de diirón cataliza la hidroboración de N-heteroarenos utilizando pinacolborano. Este proceso produce productos N-borilados y 1,2-reducidos altamente regioselectivos, con la escisión de enlaces B-H como el paso clave para determinar la tasa.

Área de la Ciencia:

Química organometálica
Catálisis
Síntesis orgánica

Sus antecedentes:

Los N-heteroarenos son motivos estructurales importantes en productos farmacéuticos y materiales.
Los métodos eficientes para su funcionalización selectiva son muy buscados.
La hidroboración ofrece una vía versátil para introducir grupos que contienen boro.

Objetivo del estudio:

Desarrollar un nuevo sistema catalítico para la hidroboración de N-heteroarenos.
Investigar la actividad catalítica y la selectividad de un complejo diirónico.
Para aclarar el mecanismo de la reacción de hidroboración.

Principales métodos:

Síntesis y caracterización de un complejo de diironio con puente N2: [Cp*(Ph2PC6H4S) Fe]2(μ-N2) (1).
Hidroboración catalítica de varios N-heteroarenos mediante el uso de pinacolborano.
Estudios mecánicos para determinar el paso determinante de la velocidad.

Principales resultados:

El complejo de diirón (1) cataliza efectivamente la hidroboración de los N-heteroarenos.
La reacción produce productos 1,2-reducidos borilados con alta regioselectividad.
El inicio de la catálisis implica la coordinación de N-heteroareno con el centro de hierro.
El clivado de bonos B-H fue identificado como el paso determinante de la tasa.

Conclusiones:

Un nuevo catalizador de diironio permite una hidroboración eficiente y regioselectiva de los N-heteroarenos.
El estudio proporciona información sobre el mecanismo catalítico, destacando la escisión del enlace B-H como crucial.
Este trabajo ofrece una valiosa herramienta sintética para acceder a derivados funcionalizados de N-heteroareno.

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