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Conversión directa de compuestos de carbonilo en haluros orgánicos: desoxigenación halogenada catalizada por

Yoshiyuki Onishi¹, Daigo Ogawa, Makoto Yasuda

¹Department of Molecular Chemistry and Handai Frontier Research Center, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.

Journal of the American Chemical Society

|November 15, 2002

Resumen

El hidróxido de indio (III) cataliza efectivamente la cloración desoxigenativa de los carbonilos mediante el uso de clorodimetilsilano. Este nuevo método ofrece una conversión quimioselectiva, preservando varios grupos funcionales.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis es la catálisis.
Química del organosilicio Química del organosilicio

Sus antecedentes:

Los compuestos de carbonilo son versátiles intermedios sintéticos.
Las transformaciones desoxigenativas ofrecen rutas eficientes a las moléculas funcionalizadas.
El desarrollo de catalizadores selectivos para la funcionalización del carbonilo sigue siendo un desafío clave.

Objetivo del estudio:

Desarrollar un nuevo sistema catalítico para la cloración desoxigenativa de carbonilos.
Para investigar la actividad catalítica del hidróxido de indio (III) en esta transformación.
Para dilucidar el mecanismo de reacción y explorar el alcance del sustrato.

Principales métodos:

Reacción de varios compuestos de carbonilo con el clorodimetilsilano.
Catálisis con el uso de hidróxido de indio (In) (OH) 3).
Análisis de los productos de reacción y estudios mecanicistas.

Principales resultados:

El hidróxido de indio (III) catalizó selectivamente la cloración desoxigenativa de los carbonilos para obtener los productos correspondientes.
La reacción procedió a través de la hidrociliación inicial seguida de la cloración.
El catalizador de indio demostró quimioselectividad, dejando intactos los grupos éster, nitro, ciano y halógeno.
Otros nucleófilos como el alilo y el yodo también fueron compatibles.

Conclusiones:

El hidróxido de indio (III) es un catalizador único y eficaz para la cloración desoxigenativa de los carbonilos.
La metodología desarrollada proporciona una ruta quimioselectiva para la introducción de nucleófilos de hidrógeno y cloro en el carbono carbonilo.
Esta reacción expande la utilidad sintética de los reactivos de organosilicio en la síntesis orgánica.

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