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Arilboración Ni-Catalizada de Alquenos No Activados: Estudios de Alcance y Mecanismos

Stephen R Sardini¹, Alison L Lambright¹, Grace L Trammel¹

¹Department of Chemistry , Indiana University , 800 East Kirkwood Avenue , Bloomington , Indiana 47405 , United States.

Journal of the American Chemical Society

|June 12, 2019

Resumen

Este estudio introduce un nuevo método de arilboración catalizada por níquel para crear moléculas complejas. La reacción sintetiza eficientemente valiosos enlaces carbono-boro en alquenos altamente sustituidos, ofreciendo control sobre la estereoselectividad y la regioselectividad.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Las reacciones de arilboración son cruciales para la formación de enlaces C-C.
La síntesis de alquenos altamente sustituidos con estereoquímica controlada sigue siendo un desafío.
El desarrollo de métodos eficientes para la creación de enlaces carbono-boro es esencial para la síntesis orgánica.

Objetivo del estudio:

Para desarrollar un nuevo método de arilboración catalizado por níquel.
Para permitir la síntesis de moléculas complejas a partir de alquenos y bromuros de arilo no activados.
Para investigar los detalles mecánicos de la nueva reacción.

Principales métodos:

Arilboración catalizada por níquel de varios alquenos (monosubstituidos, 1,1-disubstituidos y trisubstituidos).
Se utilizan bromuros de arilo y reactivos de diboro.
Empleó técnicas computacionales y experimentales para estudiar los mecanismos de reacción.

Principales resultados:

Arilboración exitosa de alquenos no activados y altamente sustituidos.
Formación de productos con un centro de carbono cuaternario y un enlace versátil carbono-boro.
Control demostrado de la estereoselectividad y la regioselectividad.
Aplicación en la síntesis de heterociclos de nitrógeno saturado.

Conclusiones:

El método desarrollado catalizado por Ni proporciona una ruta eficiente a compuestos de arilborón sintéticamente valiosos.
La metodología es aplicable a la síntesis de importantes motivos farmacéuticos.
Los estudios mecánicos proporcionan información sobre la reactividad y la selectividad inusuales de la reacción.

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