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Oxidación de los organotrifluoroboratos sustituidos por hidroxilo
Gary A Molander1, Daniel E Petrillo
1Roy and Diana A. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Journal of the American Chemical Society
|July 27, 2006
Resumen
Nuevos organotrifluoroboratos con grupos hidroxilo fueron sintetizados y oxidados. Estos compuestos muestran excelentes rendimientos y son útiles en las reacciones de acoplamiento cruzado Suzuki-Miyaura.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química organometálica Química orgánica de los metales.
Sus antecedentes:
- Los organotrifluoroboratos son unos versátiles intermediarios sintéticos.
- Los grupos hidroxilo pueden complicar las transformaciones sintéticas.
Objetivo del estudio:
- Desarrollar un método para la oxidación de organotrifluoroboratos con grupos hidroxilo.
- Para evaluar la utilidad de los productos oxidados en las reacciones de acoplamiento cruzado.
Principales métodos:
- Síntesis de organotrifluoroboratos de potasio y tetra-n-butilamonio con grupos hidroxilo.
- Oxidación de estos compuestos utilizando oxidantes comunes.
- Reacciones de acoplamiento cruzado Suzuki-Miyaura de los productos oxidados.
Principales resultados:
- Los organotrifluoroboratos con grupos hidroxilo primarios y secundarios fueron oxidados con éxito.
- Se lograron rendimientos de moderados a excelentes con la retención completa de la fracción de trifluoroborato.
- Los productos oxidados participaron efectivamente en el acoplamiento cruzado Suzuki-Miyaura.
Conclusiones:
- Se estableció un método robusto para la oxidación de organotrifluoroboratos que contienen hidroxilo.
- La porción de trifluoroborato es estable bajo las condiciones de oxidación.
- Estos organotrifluoroboratos oxidados son bloques de construcción valiosos para la síntesis orgánica.
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