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Regioselectivo [2 + 2 + 2] mediado por níquel, cicloadición de carboreno con alquinos

Liang Deng¹, Hoi-Shan Chan, Zuowei Xie

¹Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territory, Hong Kong, China.

Journal of the American Chemical Society

|June 15, 2006

Resumen

Este estudio introduce una nueva reacción catalizada por níquel para la síntesis de benzocarboranos complejos. La nueva química del carboreno ofrece un método regioselectivo para crear valiosos compuestos orgánicos.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
Química del carborano Química del carborano
Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

Los complejos de metales de transición-benceno son ampliamente utilizados en la síntesis y la ciencia de los materiales.
La química de los complejos de metales de transición-carborina, particularmente con metales de transición tardía, sigue siendo en gran parte inexplorada.

Objetivo del estudio:

Para informar de una nueva reacción de cicloadición regioselectiva [2 + 2 + 2] mediada por níquel que involucra carboreno.
Para explorar la formación y la reactividad de los intermediarios de níquel-carborina.

Principales métodos:

Generación de un intermediario de níquel-carborino, (eta2-C2B10H10) Ni (PPh3) 2.
Reacción del intermedio con varios alcinos, incluidos los asimétricos.

Principales resultados:

Cícloadición regioselectiva [2 + 2 + 2] exitosa de carboreno con alquinos.
Se observó una alta regioselectividad debido al grueso estérico de la fracción de carborano.
Síntesis de benzocarboranos altamente sustituidos que antes eran difíciles de obtener.

Conclusiones:

Se ha establecido una nueva ruta sintética para obtener benzocarboranos altamente sustituidos.
Este trabajo amplía la química conocida de los complejos de metal de transición-carborina.
La influencia estérica del grupo carborano puede controlar la regioselectividad en las reacciones de cicloadición.

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