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Ciclopropanación fotocatalítica redox-neutral mediante el cruce radical/polar
James P Phelan1, Simon B Lang1, Jordan S Compton1
1Roy and Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States.
Journal of the American Chemical Society
|June 20, 2018
Resumen
Un nuevo reactivo estable permite una ciclopropanación eficiente de las olefinas impulsada por la luz visible. Este método es compatible con diversos grupos funcionales, ofreciendo una herramienta versátil para la síntesis orgánica.
Área de la Ciencia:
- Química orgánica
- Metodología sintética
- Fotocatálisis
Sus antecedentes:
- La ciclopropanación es una transformación clave en la síntesis orgánica.
- El desarrollo de reactivos estables y fáciles de usar para una ciclopropanación eficiente sigue siendo un área activa de investigación.
Objetivo del estudio:
- Desarrollar un nuevo reactivo estable para la ciclopropanación redox-neutral.
- Establecer un protocolo mediado por luz visible para la ciclopropanación de olefinas.
Principales métodos:
- Síntesis de trietilamonio bis (catécolato) iodometilsilicato
- Fotocatálisis por ciclopropanación con luz visible y un fotocatalizador orgánico.
- Estudios mecanicistas que incluyen análisis experimentales y computacionales.
Principales resultados:
- Se sintetizó con éxito un reactivo estable y bifuncional para la ciclopropanación en una escala multigrama.
- La ciclopropanación eficiente de varias olefinas, incluidos los sustratos difíciles, se logró en cuestión de horas.
- La reacción demostró alta tolerancia funcional del grupo y quimioselectividad.
Conclusiones:
- El reactivo desarrollado y el método fotocatalítico proporcionan un enfoque potente y versátil para la ciclopropanación de olefinas.
- La reacción se produce a través de un mecanismo de cierre de anillo aniónico 3-exo-tet.
- Esta metodología ofrece ventajas significativas para sintetizar moléculas complejas.
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