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Síntesis catalizada por el cobre de azoles. El estudio de DFT predice una reactividad y productos intermedios sin
Fahmi Himo1, Timothy Lovell, Robert Hilgraf
1Department of Molecular Biology, The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Journal of the American Chemical Society
|January 6, 2005
Resumen
El cobre ((I) los acetiluros alteran el Huisgen.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis es la catálisis.
- Mecanismos de reacción Mecanismos de reacción
Sus antecedentes:
- Las cicloadiciones 1,3-dipolares de Huisgen son típicamente reacciones concertadas.
- La catálisis del cobre es ampliamente utilizada en la síntesis orgánica.
Objetivo del estudio:
- Para investigar el mecanismo de las reacciones catalizadas por el cobre entre acetílidos y dipolos.
- Explorar el alcance y la confiabilidad de estas adiciones cíclicas.
Principales métodos:
- Reacciones de cicloadición catalizadas por el cobre (I).
- Estudios computacionales (por ejemplo, DFT) para dilucidar las vías de reacción.
Principales resultados:
- Los acetílidos de cobre (I) inducen mecanismos de cicloadición no concertados.
- Formación de 1,4-disubstituidos 1,2,3-triazoles y 3,4-disubstituidos isoxazoles.
- Identificación de los intermediarios comunes del ciclo del metal.
Conclusiones:
- La catálisis del cobre transforma las cicloadiciones de Huisgen en procesos escalonados.
- La reacción ofrece una ruta confiable a los triazoles y isoxazoles sustituidos.
- Los intermediarios del ciclo del metal son clave para esta transformación.
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