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N-Carbenos Heterocíclicos Estabilizados y 1-Bora-1,3-butadienos

Chaohuang Chen¹, Constantin G Daniliuc¹, Gerald Kehr¹

¹Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.

Journal of the American Chemical Society

|December 13, 2021

Resumen

Se sintetizaron y caracterizaron 1-bora-1,3-butadienos estabilizados por NHC. Estos compuestos sufren diversas reacciones que incluyen hidroboración, calcogenación y complejación con metales de transición, produciendo nuevos productos cíclicos y organometálicos.

Área de la Ciencia:

Química organometálica
Química del boro
Síntesis orgánica

Sus antecedentes:

Los carbenos N-heterocíclicos (NHC) son ligandos versátiles en la química organometálica.
Los compuestos que contienen boro exhiben una reactividad y propiedades estructurales únicas.

Objetivo del estudio:

Para sintetizar y explorar la reactividad de 1-bora-1,3-butadienos estabilizados por NHC.
Investigar la utilidad de estos nuevos compuestos de boro en las transformaciones orgánicas y la formación de complejos metálicos.

Principales métodos:

Deprotonación de cationes de borenio para generar 1-bora-1,3-butadienos.
Reacciones de hidroboración con HB ((C6F5) 2).
1,4-calcogenación con azufre y selenio elementales.
Reacciones con dióxido de azufre.
Complejación con los precursores de rutenio y rodio.

Principales resultados:

Síntesis de s-trans-1-bora-1,3-butadienos planos estabilizados por los ligandos del NHC.
Formación de enolados/enamidas cíclicos de boro-borato de zwitterión mediante hidroboración y captura.
Síntesis de productos heterocíclicos de seis miembros mediante adición de 1,4 con SO2.
Generación de ligandos eta3-alilo borilados y complejos Rh, incluidos los productos de activación C-H intramolecular.

Conclusiones:

Los 1-bora-1,3-butadienos estabilizados por NHC son bloques de construcción accesibles y versátiles.
Estos compuestos permiten nuevas vías sintéticas a diversas estructuras organobóricas y organometálicas.
El estudio amplía el alcance de la química del boro y sus aplicaciones en la catálisis y la ciencia de los materiales.

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