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Un método general para la arilación catalizada por el cobre de los enlaces C-H del areno

Hien-Quang Do¹, Rana M Kashif Khan, Olafs Daugulis

¹Department of Chemistry, University of Houston, Houston, Texas 77204-5003, USA.

Journal of the American Chemical Society

|October 16, 2008

Resumen

Un nuevo método catalizado por cobre permite la arilación de enlaces C-H en varios heterociclos y arenas utilizando haluros de arilo. Este avance expande las posibilidades sintéticas para la construcción de moléculas complejas.

Área de la Ciencia:

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

Sus antecedentes:

La funcionalización del enlace C-H es crucial en la síntesis orgánica.
La catálisis del cobre ofrece una plataforma versátil para reacciones de acoplamiento cruzado.

Objetivo del estudio:

Desarrollar un método general catalizado por el cobre para la arilación de enlaces sp(2) C-H.
Ampliar el alcance de los sustratos susceptibles a la arilación C-H.

Principales métodos:

Reacción de acoplamiento cruzado catalizada por cobre.
Utilizó haluros de arilo como socios de acoplamiento.
Se utiliza el alcóxido de litio o el fosfato de potasio (K3PO4) como base en varios disolventes como DMF, DMPU o DMF / xilenos.

Principales resultados:

Los heterociclos ricos en electrones y pobres en electrones arillados con éxito (por ejemplo, azoles, cafeína, tiofenos, benzofuranos, óxidos de piridina, piridazina, pirimidina).
Se logra la arilación de arenas pobres en electrones con al menos dos grupos de retirada de electrones.
Sintetizó dos compuestos intermedios del complejo arilcobre-fenantrolina.

Conclusiones:

El método desarrollado proporciona un enfoque general para la arilación C-H catalizada por cobre.
La metodología es efectiva para una amplia gama de sustratos heterocíclicos y aromáticos.
La síntesis de complejos intermedios proporciona conocimientos mecanicistas.

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