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La olefinación C-H dirigida por N-nitroso y catalizada por el rodio (III) de los arenos. Acoplamiento versátil de

Baoqing Liu¹, Yang Fan, Yang Gao

¹Department of Polymer Science and Engineering, School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, China.

Journal of the American Chemical Society

|December 13, 2012

Resumen

Los investigadores desarrollaron un nuevo método catalizado por Rh para la ortoolefinación de arenas utilizando compuestos N-nitroso. Esta versátil estrategia dirigida por N-nitroso ofrece condiciones suaves, altos rendimientos y un amplio alcance de sustrato para la síntesis orgánica.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis es la catálisis.
Metodología sintética de la metodología sintética.

Sus antecedentes:

Los compuestos N-nitroso son estructuras orgánicas versátiles con reactividades demostradas.
El desarrollo de metodologías sintéticas eficientes es crucial para acceder a diversas arquitecturas químicas.

Objetivo del estudio:

Desarrollar una metodología dirigida a N-nitroso catalizada por Rh (III) para la ortoolefinación de arenas.
Explorar la utilidad sintética y los fundamentos mecanicistas de esta nueva transformación.

Principales métodos:

Se utilizó la catálisis de Rh (III) para la ortoolefinación dirigida por N-nitroso.
Se llevaron a cabo estudios mecanicistas integrales que incluyen el intercambio de deuterio, el efecto de isótopos cinéticos y el perfil cinético.
Investigó varios complejos de Rh (III) y las condiciones de reacción.

Principales resultados:

Se lograron condiciones de reacción suaves y altos rendimientos para la ortoolefinación de arenas.
Compatibilidad sintética demostrada con sustratos difíciles, incluidas las olefinas no activadas como el 1-octeno.
Se estableció el estado de reposo del catalizador como [RhCp*](2+), la activación electrofílica de C-H como el paso que limita el volumen de negocios, y un intermediario de cinco miembros del ciclo rodado.

Conclusiones:

El grupo N-nitroso dirige la ortoolefinación bajo condiciones ligeramente catalizadas por Rh (III).
Esta metodología proporciona acceso a valiosas arquitecturas orgánicas con un amplio alcance de sustrato.
La fracción N-nitroso puede transformarse aún más en funcionalidades de aminas, destacando su versatilidad sintética.

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