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Una estrategia de grupo de dirección transitoria permite la síntesis de organofluoro multicomponente enantioselectiva

Zhonglin Liu¹, Lucas J Oxtoby¹, Mingyu Liu¹

¹Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of the American Chemical Society

|June 2, 2021

Resumen

Este estudio introduce un nuevo método catalizado por el paladio para crear fluorofuncionalización vicinal en alquenos. La eficiente reacción de acoplamiento de tres componentes ofrece una alta selectividad para las valiosas moléculas fluoradas.

Área de la Ciencia:

Química orgánica
Catálisis
Química del fluor

Sus antecedentes:

La fluorofuncionalización vicina de los alquenos es crucial para la síntesis de compuestos fluorados.
Los métodos existentes a menudo carecen de un amplio alcance y una selectividad precisa.

Objetivo del estudio:

Desarrollar un método novedoso y selectivo para la fluorofuncionalización de alceno.
Para lograr una alta regioselectividad, diastereoselectividad y enantioselectividad en la síntesis de moléculas fluoradas vecinas.

Principales métodos:

Utilizó una reacción de acoplamiento de tres componentes catalizada por paladio.
Se utilizan alquenilbenzaldehídos, ácidos arilborónicos y un agente fluorante (N-fluoro-2,4,6-trimetilpiridinio hexafluorofosfato).
Incorporó un grupo de dirección transitorio para controlar la selectividad del sitio.

Principales resultados:

Se han sintetizado con éxito compuestos fluorados con un excelente control estéreo.
Se han demostrado elevadas regioselectividades, diastereoselectividades y enantioselectividades en la reacción de acoplamiento.
La metodología permite la construcción de moléculas fluoradas complejas.

Conclusiones:

El método descrito proporciona una vía eficiente y selectiva para la fluorofuncionalización vicinal.
Este enfoque amplía el conjunto de herramientas sintéticas para acceder a valiosos compuestos orgánicos fluorados.
Los productos resultantes son andamios relevantes para el desarrollo de moléculas bioactivas.

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