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Hidroformilación asimétrica de olefinas sin disolventes catalizada por un complejo de poliestireno soportado por

Fumitoshi Shibahara¹, Kyoko Nozaki, Tamejiro Hiyama

¹Conversion and Control by Advanced Chemistry, PRESTO, Japan Science and Technology, 1-8, Honcho 4-Chome, Kawaguchi 332-0012, Japan.

Journal of the American Chemical Society

|July 10, 2003

Resumen

Este estudio demuestra la hidroformilación asimétrica sin disolventes utilizando un catalizador soportado por polímeros. Este método convierte eficientemente varias olefinas en valiosos aldehídos quirales con alta selectividad y enantioselectividad.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Química verde es la química verde.

Sus antecedentes:

La hidroformilación asimétrica es crucial para la síntesis de aldehídos quirales.
Los métodos tradicionales a menudo se basan en catalizadores homogéneos y disolventes orgánicos, lo que plantea desafíos ambientales y de separación.

Objetivo del estudio:

Desarrollar un proceso de hidroformilación asimétrico sin disolventes utilizando un catalizador reciclable apoyado en polímeros.
Para investigar la eficacia del catalizador a través de diferentes sustratos de olefinas y tipos de reactores.

Principales métodos:

Anclaje covalente de un complejo (R,S) -BINAPHOS-Rh{I} a un soporte de poliestireno.
Realización de hidroformilación asimétrica en reactores por lotes y de flujo continuo (flujo de vapor y CO2 supercrítico).
Utilizando sustratos olefinos gaseosos y líquidos, incluidos el cis-2-buteno, el 3,3,3-trifluoropropeno, el estireno y el acetato de vinilo.

Principales resultados:

Se logró un 100% de regioselectividad y un 82% de exceso enantiomérico (ee) para (S)-2-metilbutanal a partir de cis-2-buteno.
Convirtió 3,3,3-trifluoropropeno en (S)-2-trifluorometilpropanal con una proporción 95/5 iso/normal y un 90% ee.
Sintetizó con éxito varios isoaldehídos ópticamente activos a partir de diversas olefinas con altos valores de ee.

Conclusiones:

El catalizador soportado por polímeros permite una hidroformilación asimétrica eficiente y libre de disolventes.
El sistema desarrollado es versátil, aplicable a diferentes configuraciones de reactores y tipos de olefinas.
Este enfoque facilita la creación de bibliotecas de aldehído quiral, lo que hace avanzar la química sintética.

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