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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

La oxyalquilación de alqueno habilitada mediante la fusión de la catálisis del renio con reactivos hipervalentes de

Yin Wang¹, Lei Zhang, Yunhui Yang

¹Beijing National Laboratory of Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, China.

Journal of the American Chemical Society

|November 19, 2013

Resumen

Los catalizadores de renio permiten una nueva oxyalquilación de alquenos utilizando reactivos hipervalentes de yodo (III). Este método introduce oxígeno y grupos alquilo simultáneamente a través de la descarboxilación, ofreciendo una vía sintética versátil.

Área de la Ciencia:

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

Sus antecedentes:

Las reacciones de oxyalquilación son cruciales para sintetizar moléculas orgánicas funcionalizadas.
El desarrollo de métodos de difuncionalización eficientes y selectivos para alquenos sigue siendo un desafío clave en la síntesis orgánica.

Objetivo del estudio:

Para desarrollar una nueva oxyalquilación catalizada por renio de alquenos.
Para utilizar reactivos hipervalentes de yodo (III) como fuentes de oxigenación y alquilación duales a través de la descarboxilación.

Principales métodos:

La catálisis de renio fue empleada para la reacción de oxyalquilación.
Se utilizaron reactivos hipervalentes de yodo (III) derivados de ácidos carboxílicos alifáticos.
Se llevaron a cabo estudios mecanicistas que involucraron descarboxilación, adición de radicales y captura de cationes.

Principales resultados:

La reacción logró un amplio alcance de sustrato y una difuncionalización totalmente específica de la región.
Se utilizaron condiciones de reacción leves y sustratos fácilmente disponibles.
Se aclaró un mecanismo en cascada de descarboxilación/adición de radicales/atrapamiento de cationes.

Conclusiones:

Se ha establecido una nueva y eficiente oxyalquilación catalizada por renio de alquenos.
Los reactivos hipervalentes de yodo (III) sirven como fuentes efectivas de oxigenación y alquilación duales.
La reacción procede a través de un mecanismo en cascada único, ofreciendo una valiosa herramienta sintética.

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