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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

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Bromuros de alquilo como fuentes leves de hidróxido en la hidroamidación de alquinos con isocyanatos catalizados por

Xueqiang Wang¹, Masaki Nakajima¹, Eloisa Serrano¹

¹Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology , Av. Països Catalans 16, 43007 Tarragona, Spain.

Journal of the American Chemical Society

|December 10, 2016

Resumen

Este estudio introduce una nueva reacción de hidroamidación catalítica para la fabricación de acrilamidas. El método innovador utiliza eficientemente los bromuros de alquilo, transformando un proceso químico común en una herramienta sintética valiosa.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Las reacciones de hidroamidación son cruciales para sintetizar compuestos de amida valiosos.
La eliminación de β-hidruro es a menudo una reacción secundaria indeseable en los procesos catalíticos.

Objetivo del estudio:

Desarrollar una nueva hidroamidación catalítica de alquinas con isocyanatos.
Para utilizar los bromuros de alquilo como fuentes eficientes de hidrógeno.
Para aprovechar la eliminación de β-hidruro como un paso mecánico clave.

Principales métodos:

Reacción de hidroamidación catalítica.
Uso de bromuros de alquilo como donantes de hidrógeno.
Optimización de la reacción para la quimioselectividad y la regioselectividad.

Principales resultados:

Desarrollo exitoso de una hidroamidación catalítica de alquinas e isocyanatos.
Demostración de los bromuros de alquilo como fuentes efectivas de hidrógeno.
Síntesis rápida de acrilamidas con alta quimio y regioselectividad.

Conclusiones:

El método desarrollado ofrece una ventaja estratégica al utilizar la eliminación de β-hidruro.
Este enfoque proporciona una ruta eficiente para las acrilamidas funcionalizadas.
La reacción es una valiosa adición a la química orgánica sintética.

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