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Tiocarbonilación regioselectiva de los arenos vinílicos

Vera Hirschbeck¹, Paul H Gehrtz¹, Ivana Fleischer¹

¹Institute of Organic Chemistry, University of Regensburg , Universitätsstraße 31, D-93053 Regensburg, Germany.

Journal of the American Chemical Society

|December 15, 2016

Resumen

Este estudio introduce una nueva tiocarbonilación catalizada por el paladio para sintetizar tioésteres a partir de derivados del estireno. El método logra una alta regioselectividad para el isómero ramificado en condiciones suaves, ofreciendo una ruta sintética valiosa.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

La síntesis del tioester es crucial en la química orgánica.
Los métodos existentes a menudo carecen de regioselectividad o requieren condiciones duras.

Objetivo del estudio:

Desarrollar una nueva tiocarbonilación catalizada por el paladio de derivados del estireno.
Para lograr una alta regioselectividad para el isómero tioester ramificado.
Para establecer condiciones de reacción suaves y eficientes.

Principales métodos:

Reacción catalizada por el paladio con derivados de estireno y tiolos.
El uso de un ligando bidentado para mejorar la reactividad y la selectividad.
Utilizando un sustituto de monóxido de carbono (CO) por seguridad y comodidad.

Principales resultados:

Primer informe de la tiocarbonilación catalizada por el paladio de los estirenos.
Se obtiene una alta regioselectividad, favoreciendo el isómero ramificado.
Amplia tolerancia del grupo funcional tanto en sustratos de areno como de tiol.
Conversión exitosa de estirenos orto-sustituidos desafiantes.

Conclusiones:

Este método proporciona una vía versátil y eficiente para los tioésteres.
La reacción se lleva a cabo en condiciones ambientales suaves con baja carga de catalizador.
El protocolo desarrollado ofrece una nueva reactividad y una alta regioselectividad, en particular para sustratos estéricamente obstaculizados.

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