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Reacción asimétrica de acoplamiento de tres componentes catalizada por Pd/GF para el acceso a diarilmetilalquinas

Guofeng Zhao¹, Yi Wu¹, Hai-Hong Wu¹

¹Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, People's Republic of China.

Journal of the American Chemical Society

|October 26, 2021

Resumen

Los investigadores desarrollaron una nueva reacción de acoplamiento catalizada por Pd para crear diarilmetilalquinas quirales. Este método utiliza materiales de partida fácilmente disponibles y un nuevo ligando quiral, que ofrece una forma sencilla de sintetizar compuestos orgánicos valiosos.

Área de la Ciencia:

Química orgánica
Catálisis
Síntesis asimétrica

Sus antecedentes:

Las transformaciones selectivas de las N-tosilhidrazonas son importantes en la síntesis orgánica.
El desarrollo de métodos enantioselectivos para estas transformaciones presenta desafíos significativos.

Objetivo del estudio:

Para reportar una nueva reacción de acoplamiento de tres componentes enantioselectiva catalizada por Pd.
Proporcionar un fácil acceso a las diarilmetilalquinas quirales utilizando un nuevo ligando quiral.

Principales métodos:

Utilizó una reacción de acoplamiento de tres componentes catalizada por paladio.
Se empleó un nuevo ligando quiral de la sulfinamida fosfina (GF-Phos).
N-tosilhidrazona reaccionada, haluro de arilo y alquino terminal bajo condiciones suaves.

Principales resultados:

Se han sintetizado con éxito diarilmetilalquinas quirales de alta enantioselectividad.
Se ha demostrado que se puede acceder a ambos enantiómeros del producto utilizando el mismo ligando.
Demostró el alcance general del sustrato y la facilidad de ampliación.

Conclusiones:

El método desarrollado ofrece una ruta versátil y eficiente a valiosas sintonas quirales.
La reacción se caracteriza por condiciones suaves, materiales de partida fácilmente disponibles y alta enantioselectividad.
Este enfoque facilita la síntesis de moléculas que contienen el andamio diarilmetilalquina, relevante para los compuestos bioactivos.

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