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Los fosfalamirenos: síntonos para los heterociclos del grupo principal

Liu Leo Liu¹, Jiliang Zhou¹, Levy L Cao¹

¹Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , Ontario M5S 3H6 , Canada.

Journal of the American Chemical Society

|September 27, 2019

Resumen

Se sintetizaron nuevos fosfalauminirenos con un anillo de aluminio-carbono-fosforo (AlCP) de tres miembros tensados. Estos compuestos se someten a reacciones de apertura y ampliación del anillo, formando nuevos heterociclos del grupo principal.

Área de la Ciencia:

Química organometálica
Química del grupo principal
Química sintética

Sus antecedentes:

Los complejos de aluminio son productos intermedios reactivos.
Las fosfalicinas son bloques de construcción versátiles en síntesis.
Los anillos de tres miembros a menudo exhiben una reactividad única debido a la tensión.

Objetivo del estudio:

Para sintetizar nuevos fosfalamirenos que contienen un anillo de tres miembros de AlCP.
Investigar la reactividad y la aromaticidad de estos sistemas de AlCP tensados.
Explorar la formación de nuevos heterociclos del grupo principal.

Principales métodos:

[1 + 2] reacción de cicloadición entre un complejo de aluminio (I) y fosfaquinos.
Síntesis de compuestos cristalinos de fosfalauminireno.
Cálculos de la teoría funcional de la densidad (DFT) para conocimientos mecanicistas.
Reacciones con varios sustratos (alcoholes, isocyanuros, carbenos, calcógenos, carbonilos, nitriles) para estudiar la apertura y el agrandamiento del anillo.

Principales resultados:

Síntesis de los fosfalamirenos HC[(CMe) ((NDipp) ]2Al[C(R) P] (2 y 3).
Pruebas computacionales para la aromaticidad de 2π-electrones en el anillo AlCP.
Apertura del anillo del compuesto 3 tras la protonación para producir el fosfalqueno 4.
Facil ampliación del anillo del compuesto 3 con diversos reactivos (CyNC, BAC, Se, Ph2CO, PhCHCHCOPh, PhCN) para formar heterociclos del grupo principal sin precedentes 5-10.
Preservación del enlace insaturado CP en los heterociclos recién formados.

Conclusiones:

Los fosfalauminirenos con anillos de AlCP tensados son accesibles a través de la cicloadición [1 + 2].
El anillo de AlCP exhibe un carácter aromático y sufre diversas reacciones de apertura y ampliación del anillo.
Esta química proporciona acceso a nuevos heterociclos del grupo principal con enlaces CP intactos.

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