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Síntesis de sulfuro de arilo catalizado por Ni a través de una reacción de intercambio de arilo
Ryota Isshiki1, Miki B Kurosawa1, Kei Muto2
1Department of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo 162-0041, Japan.
Journal of the American Chemical Society
|June 28, 2021
Resumen
Este estudio presenta un nuevo método catalizado por níquel para sintetizar sulfuros de arilo utilizando reacciones de intercambio de arilo. Este enfoque evita los tiolos peligrosos al emplear el 2-piridil sulfuro como una fuente de sulfuro más segura.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Metodología sintética
Sus antecedentes:
- La síntesis tradicional de sulfuro de arilo a menudo involucra tiolos tóxicos y maloloros.
- El desarrollo de rutas sintéticas más seguras y eficientes es crucial en la química orgánica.
Objetivo del estudio:
- Desarrollar un nuevo método catalizado por níquel para la síntesis de sulfuro de arilo.
- Para utilizar una reacción de intercambio de arilo para evitar el uso de tiolos.
- Para explorar el alcance de los electrófilos arilo en esta transformación.
Principales métodos:
- Reacción de intercambio de arilo catalizada por un sistema de níquel/dcipto.
- Utilizando el 2-piridil sulfuro como donante de sulfuro.
- Empleando varios electrófilos de arilo que incluyen ésteres aromáticos, derivados de arenol y haluros de arilo.
Principales resultados:
- Síntesis exitosa de sulfuros de arilo a través del intercambio de arilo catalizado por níquel.
- Se ha demostrado que se evitan los tiolos olorosos y tóxicos mediante el uso de 2-piridil sulfuro.
- El catalizador Ni/dcypt se divide efectivamente y forma enlaces aril-S.
- Los estudios mecanicistas indicaron adiciones oxidativas y intercambio de ligandos simultáneos.
Conclusiones:
- Se ha establecido un método nuevo y más seguro para la síntesis de sulfuro de arilo.
- El método desarrollado ofrece una valiosa alternativa a los enfoques tradicionales basados en tiol.
- El catalizador Ni/dcypt juega un papel crítico en la facilitación del mecanismo de intercambio de arilo.
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