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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Acoplamiento cruzado directo C-H habilitado por la generación catalítica de radicales de cloro

Benjamin J Shields¹, Abigail G Doyle¹

¹Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.

Journal of the American Chemical Society

|September 23, 2016

Resumen

Este estudio introduce un nuevo método catalizado por níquel y fotorreducción para el acoplamiento cruzado C ((sp3) -H. El proceso arila de manera eficiente los éteres utilizando cloruros de arilo, lo que permite una amplia funcionalización de C ((sp3) -H en condiciones suaves.

Área de la Ciencia:

Química orgánica
Catálisis
La fotoquímica

Sus antecedentes:

La funcionalización del enlace C-sp3H es crucial en la síntesis orgánica.
El desarrollo de métodos suaves y eficientes para la arilación C ((sp3) -H sigue siendo un desafío importante.

Objetivo del estudio:

Desarrollar una plataforma catalítica novedosa para el acoplamiento cruzado C ((sp3) -H.
Para permitir la arilación de éteres utilizando cloruros de arilo como socios de acoplamiento y precursores de radicales.

Principales métodos:

Utilizó una combinación de níquel y fotorreducción por catálisis.
Cloruros de arilo utilizados para la generación catalítica de radicales de cloro.
Se han investigado vías mecanicistas que implican productos intermedios de Ni (III) y fotólisis.

Principales resultados:

Se ha logrado con éxito la arilación α-óxido C ((sp3) -H de éteres cíclicos y acíclicos.
Demostró la funcionalización de los enlaces bencílicos C ((sp3) -H en el tolueno.
Se ha demostrado la arilación de enlaces C ((sp3) -H no activados en el ciclohexano.

Conclusiones:

Desarrolló una plataforma versátil de acoplamiento cruzado C ((sp3) -H.
El método funciona en condiciones excepcionalmente suaves.
Ofrece amplias implicaciones para diversas funcionalizaciones de enlaces C ((sp3) -H.

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