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Cascada de cobre catalizado 1,2,3-Trifuncionalización de las terminales Allenes

Wanxiang Zhao¹, John Montgomery¹

¹Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States.

Journal of the American Chemical Society

|July 21, 2016

Resumen

En este estudio se introduce una catalización en cascada de cianificación/diborilación de alenos mediante el uso de bis ((pinacolato) diboro y N-ciano-N-fenil-p-metilbencensulfonamida. Este método sintetiza eficientemente diversos productos cianoborilados para futuras transformaciones químicas.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Los alenos terminales son precursores sintéticos muy versátiles.
La cianoborilación y la diborilación son reacciones de funcionalización importantes.
Se necesitan métodos catalíticos eficientes para la síntesis de moléculas complejas.

Objetivo del estudio:

Desarrollar una nueva reacción de cianificación/diborilación en cascada para los alenos terminales.
Explorar la utilidad sintética de los productos cianoborilados resultantes.

Principales métodos:

Reacción catalizada por el cobre mediante el uso de bis ((pinacolato) diboro (B2Pin2) y N-ciano-N-fenil-p-metilbenzenosulfonamida (NCTS).
Investigaciones mecanicistas, incluido el análisis intermedio.
Funcionalización posterior de los aductos a través de acoplamientos cruzados y heteroariaciones.

Principales resultados:

Síntesis eficiente de derivados de aleno cianoborilados.
Los conocimientos mecanicistas revelan una cyanoborilación seguida de una vía de hidroboración.
Acceso demostrado a diversos productos derivados a través de transformaciones posteriores.

Conclusiones:

Se ha establecido una nueva y eficiente cianización/diborilación en cascada catalizada por cobre de los allenos terminales.
La metodología desarrollada proporciona acceso a valiosos intermediarios cianoborilados.
Los productos son susceptibles a una serie de modificaciones sintéticas adicionales, ampliando su utilidad.

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