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Síntesis de éter cíclico mediante anulación deshidrogenativa dirigida catalizada por paladio en posiciones terminales

Samuel J Thompson¹, Danny Q Thach¹, Guangbin Dong¹

¹Department of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.

Journal of the American Chemical Society

|September 1, 2015

Resumen

Este estudio introduce un nuevo método catalizado por el paladio para la funcionalización de enlaces C-H no activados utilizando alcoholes. El proceso crea eficientemente varios éteres cíclicos a través de una vía de anulación dirigida.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

La funcionalización de los enlaces C-H no activados sigue siendo un desafío importante en la síntesis orgánica.
El desarrollo de métodos eficientes para la construcción de éteres cíclicos es crucial para acceder a diversas arquitecturas moleculares.

Objetivo del estudio:

Desarrollar una nueva reacción catalizada por el paladio para la funcionalización directa de enlaces C-H no activados.
Para lograr la anulación quimioselectiva con nucleófilos de alcohol interno para la síntesis de éteres cíclicos alifáticos.

Principales métodos:

Activación de C-H catalizada por paladio utilizando un grupo directivo enmascarado por oxima.
Reacción de anulación con alcoholes primarios, secundarios y terciarios atados.
Acoplamiento de alcoholes bencílicos y silílicos protegidos.

Principales resultados:

Síntesis exitosa de una gama de éteres cíclicos alifáticos con anillos de cuatro a siete miembros.
Reactividad demostrada de varios grupos hidroxilo, incluidos los alcoholes protegidos.
Se propuso un mecanismo de reacción que involucra la activación de C-H y la sustitución intramolecular de SN2.

Conclusiones:

El método desarrollado proporciona una nueva vía poderosa para sintetizar éteres cíclicos a partir de materiales de partida fácilmente disponibles.
Este enfoque amplía el alcance de la funcionalización de C-H catalizada por paladio y ofrece una herramienta valiosa para los químicos orgánicos.

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