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Pd-Catalyzed γ-C ((sp³) -H Arylación de aminas libres utilizando un grupo directivo transitorio

Yongwei Wu¹, Yan-Qiao Chen¹, Tao Liu¹

¹Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of the American Chemical Society

|November 2, 2016

Resumen

Este estudio introduce un nuevo método para la arilación C-H catalizada por el paladio de aminas primarias utilizando un nuevo grupo de dirección. El proceso eficiente permite menores cargas de catalizador y grupo de dirección, lo que permite la síntesis de compuestos heterocíclicos complejos.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

La activación de C-H catalizada por el paladio es una herramienta poderosa en la síntesis orgánica.
Los grupos de dirección son cruciales para la funcionalización de C-H selectiva por región.
El desarrollo de estrategias de grupo de dirección eficientes y versátiles sigue siendo un área activa de investigación.

Objetivo del estudio:

Desarrollar una nueva arilación γ-C(sp3)-H catalizada por el paladio de aminas primarias.
Para utilizar el 2-hidroxinicotinaldehído como grupo de dirección catalítico transitorio (TDG).
Demostrar la eficiencia y el alcance de esta nueva metodología para sintetizar compuestos heterocíclicos valiosos.

Principales métodos:

Utilizando un sistema de catalizador de paladio.
Utilizando el 2-hidroxinicotinaldehído como un grupo direccional transitorio para la arilación γ-C{\displaystyle \{sp}}} -H.
Investigación de la compatibilidad con varios yoduros de arilo heterocíclicos.

Principales resultados:

Se ha logrado una arilación eficiente de las aminas primarias catalizadas por Pd (II) γ-C (sp3) -H.
Se ha demostrado una alta eficiencia con cargas de catalizador (2%) y de grupo de dirección (4%).
Se ha demostrado la compatibilidad con los ioduros de arilo heterocíclicos.
Se han sintetizado con éxito derivados de 1,2,3,4-tetrahidronafitiridina.

Conclusiones:

El 2-hidroxinicotinaldehído sirve como un grupo directivo catalítico transitorio eficaz para la arilación C-H.
El método desarrollado ofrece una vía altamente eficiente y versátil para las aminas primarias sustituidas y los heterociclos relacionados.
Este enfoque permite la construcción rápida de arquitecturas moleculares complejas.

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