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Ir-Sustitución catalizada de ésteres de tipo propargílico con enoxisilanos
Isamu Matsuda1, Ken-ichi Komori, Kenji Itoh
1Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan. matsudai@apchem.nagoya-u.ac.jp
Journal of the American Chemical Society
|August 1, 2002
Resumen
Este estudio introduce una nueva reacción catalizada por iridio entre los acetatos propargílicos y los enoxisilanos, produciendo eficientemente cetonas beta-alquinyl. El método ofrece altos rendimientos y selectividad para varios sustratos, lo que permite nuevas vías sintéticas.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis de la catálisis.
- Metodología sintética de la metodología sintética.
Sus antecedentes:
- Los compuestos propargílicos son versátiles intermedios sintéticos.
- Los métodos eficientes para la síntesis de cetonas beta-alquinilo son valiosos en la síntesis orgánica.
- La catálisis del iridio ofrece una reactividad única para la formación de enlaces C-C.
Objetivo del estudio:
- Desarrollar un nuevo sistema catalítico para la síntesis de cetonas beta-alquinilo.
- Para investigar la reactividad de los acetatos de tipo propargílico con los enoxisilanos.
- Explorar el alcance y la selectividad de la reacción desarrollada.
Principales métodos:
- Utilizado 1 mol% de [Ir(cod) {P(OPh) 3}2]OTf como el catalizador.
- Activó el catalizador de iridio con hidrógeno molecular (H2).
- Acetatos de tipo propargílico reaccionados con enoxisilanos bajo condiciones optimizadas.
Principales resultados:
- Se obtienen rendimientos altos a excelentes de cetonas beta-alquinilo.
- Se ha demostrado una sustitución exclusiva o selectiva en el carbono de propargilo para la mayoría de los ésteres propargílicos.
- Se observó la formación predominante de productos de allenilo cuando los ésteres poseen dos grupos fenilo en el carbono de propargilo.
Conclusiones:
- La reacción catalizada por iridio desarrollada es un método eficiente para sintetizar cetonas beta-alquinilo.
- La reacción exhibe un buen control sobre la regioselectividad basada en la estructura del sustrato.
- Esta metodología proporciona una herramienta valiosa para acceder a compuestos de carbonilo alquinilados complejos.
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