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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

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Metátesis de carbonilo-olefina interrumpida mediante la transferencia de átomos de oxígeno

Jacob R Ludwig¹, Rebecca B Watson¹, Daniel J Nasrallah¹

¹Department of Chemistry, University of Michigan, Ann Arbor, MI, USA.

Science (New York, N.Y.)

|September 29, 2018

Resumen

Los investigadores descubrieron un nuevo método de formación de enlaces carbono-carbono utilizando cetonas y olefinas. Esta reacción catalizada por ácido de Brønsted crea productos de tetrahidrofluoro a través de un nuevo intermediario de oxetano, que ofrece una vía sintética distinta.

Área de la Ciencia:

Química orgánica
Química sintética
Catálisis

Sus antecedentes:

La formación de enlaces carbono-carbono es crucial en la síntesis orgánica.
Los métodos establecidos incluyen reacciones de carbonileno, Prins y metátesis.
Las cetonas y las olefinas son materiales de partida comunes y accesibles.

Objetivo del estudio:

Informar de un nuevo modo de reactividad entre carbonilos y olefinas.
Desarrollar un nuevo método para sintetizar los derivados del tetrahidrofluoreno.
Explorar distintas vías de reacción más allá de los métodos existentes.

Principales métodos:

Ciclización intramolecular catalizada por el ácido de Brønsted de las cetonas epsilon-zeta insaturadas.
Estudios mecánicos.
Los cálculos teóricos.

Principales resultados:

Se identificó una nueva reacción de carbociclado.
Los productos de tetrahidrofluoreno fueron sintetizados a través de dos nuevos enlaces carbono-carbono.
La reacción procede a través de un intermediario de oxetano transitorio que implica la transferencia de átomos de oxígeno.

Conclusiones:

Este estudio presenta una reacción fundamentalmente distinta entre los carbonilos y las olefinas.
El método desarrollado proporciona acceso a marcos policíclicos complejos.
Estos marcos son relevantes para los materiales orgánicos, los productos naturales y los productos farmacéuticos.

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