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Una ligera formación de enlaces C-O catalizada por un complejo de renio-oxo

Benjamin D Sherry¹, Alexander T Radosevich, F Dean Toste

¹Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley 94720, USA.

Journal of the American Chemical Society

|June 6, 2003

Resumen

Un nuevo método catalítico permite la síntesis suave y regioselectiva de éteres de propargilo. Este eficiente proceso utiliza un complejo de renio-oxo para formar enlaces carbono-oxígeno, tolerando diversos grupos funcionales.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis por catálisis.
Metodología sintética de la metodología sintética.

Sus antecedentes:

Los éteres de propargilo son valiosos intermediarios sintéticos.
Los métodos existentes para su síntesis a menudo requieren condiciones duras o pasos de activación previos.

Objetivo del estudio:

Desarrollar un método suave y regioselectivo para la síntesis de éteres de propargilo.
Para utilizar un catalizador tolerante al aire y a la humedad para la formación de enlaces C-O.

Principales métodos:

Acoplamiento de alcoholes de propargilo con varios alcoholes.
La catálisis mediante el uso de un complejo de renio-oxo ((dppm) ReOCl3).
No se requiere activación previa del alcohol de propargilo ni deprotonación del nucleófilo.

Principales resultados:

Síntesis regioselectiva exitosa de éteres de propargilo bajo condiciones suaves.
El catalizador de renio-oxo demostró tolerancia al aire y a la humedad.
Amplia tolerancia al grupo funcional, incluyendo haluros de arilo, olefinas, ésteres, acetalos, haluros de alquilo primarios y ésteres conjugados.
Desplazamiento preferencial del alcohol sobre otros electrófilos.

Conclusiones:

Se ha establecido un método catalítico novedoso, suave y regioselectivo para la síntesis de éter de propargilo.
El complejo de renio-oxo proporciona un catalizador eficiente y robusto para la formación de enlaces sp3-carbono-oxígeno.
La tolerancia del método a varios grupos funcionales y la quimioselectividad lo hacen ampliamente aplicable en la síntesis orgánica.

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