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Hidroaminación antimarkovnikov intermolecular de alquenos no activados con sulfonamidas habilitada por transferencia

Qilei Zhu¹, David E Graff¹, Robert R Knowles¹

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

Journal of the American Chemical Society

|December 22, 2017

Resumen

Este estudio introduce un nuevo método catalítico para la hidroaminación anti-Markovnikov de alquenos utilizando sulfonamidas. La reacción impulsada por la luz visible ofrece un enfoque versátil para sintetizar compuestos químicos valiosos.

Área de la Ciencia:

Química orgánica
Fotocatálisis
Metodología sintética

Sus antecedentes:

Las reacciones de hidroaminación son cruciales para la formación de enlaces carbono-nitrógeno.
La hidroaminación directa anti-Markovnikov de alquenos no activados sigue siendo un desafío.
El desarrollo de sistemas catalíticos eficientes para la formación de enlaces C-N es un área clave en la síntesis orgánica.

Objetivo del estudio:

Desarrollar un nuevo método catalítico para la hidroaminación anti-Markovnikov intermolecular de alquenos no activados.
Utilizar las sulfonamidas primarias y secundarias como fuentes de nitrógeno.
Para lograr esta transformación bajo condiciones suaves, impulsadas por la luz visible.

Principales métodos:

Utilizando un fotocatalizador de iridio (III).
Utilizando una base de fosfato dialquilo.
Incorporación de un donante de átomo de hidrógeno tiol.
Reacciones de conducción bajo irradiación de luz visible a temperatura ambiente.

Principales resultados:

El éxito de la hidroaminación anti-Markovnikov intermolecular de alquenos no activados con las sulfonamidas.
Demostró un amplio alcance sintético con más de 60 ejemplos.
Proporcionó conocimientos mecanicistas, sugiriendo un intermediario de radical sulfonamidilo centrado en N a través de la transferencia de electrones acoplados a protones.

Conclusiones:

El sistema catalítico desarrollado proporciona un método eficiente y versátil para sintetizar compuestos que contienen sulfonamidas.
La reacción se lleva a cabo en condiciones suaves, lo que la hace atractiva para diversas aplicaciones.
La comprensión mecanicista ayuda en el desarrollo de las reacciones fotocatalíticas de formación de enlaces C-N.

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