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Arilación cinética cruzada por electrófilos de los alcoholes bencílicos por catálisis del níquel

Peng Guo¹, Ke Wang¹, Wen-Jie Jin¹

¹State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, China.

Journal of the American Chemical Society

|December 28, 2020

Resumen

Este estudio presenta un nuevo método de acoplamiento dinámico cinético para la funcionalización directa de alcoholes mediante la catálisis del níquel. Este enfoque permite una arilación eficiente de los alcoholes bencílicos, ofreciendo una alternativa versátil para sintetizar moléculas complejas.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Las reacciones de acoplamiento cruzado catalizadas por metales son cruciales para la transformación del alcohol, pero a menudo requieren múltiples pasos.
La funcionalización directa de los alcoholes sigue siendo un desafío importante en la química sintética.

Objetivo del estudio:

Desarrollar una estrategia dinámica de acoplamiento cruzado cinético para la funcionalización directa de los alcoholes.
Demostrar una arilación catalizada por níquel de los alcoholes bencílicos con varios electrófilos (hetero) arílicos.

Principales métodos:

Reacción de arilación electrofila cruzada catalizada por el níquel.
Utilizando alcoholes bencílicos y varios electrófilos (hetero) arílicos (por ejemplo, Ar-OTf, Ar-I, Ar-Br, Ar-Cl).
Investigando el alcance del sustrato y la tolerancia del grupo funcional.

Principales resultados:

Exitosa arilación directa de los alcoholes bencílicos con una amplia gama de electrófilos (hetero) arílicos.
Alta tolerancia a diversos grupos funcionales, incluidos los aldehídos, las cetonas, los ésteres y los heterociclos.
Se ha demostrado su aplicabilidad a los alcoholes, fenoles e indoles no activados, permitiendo la síntesis de diarilmetano.

Conclusiones:

El método de acoplamiento dinámico cinético desarrollado proporciona una ruta robusta y eficiente para la funcionalización directa del alcohol.
Esta estrategia ofrece una alternativa valiosa para la construcción de diarilmetanos y tiene aplicaciones en la síntesis de moléculas bioactivas y la modificación de péptidos.

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