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Bidentato quiral de borilo ligando habilitado por catálisis de iridio asimétrica C ((sp2) -H Borilación de
Xiaoliang Zou1, Haonan Zhao1, Yinwu Li2
1State Key Laboratory for Oxo Synthesis and Selective Oxidation , Center for Excellence in Molecular Synthesis, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, University of Chinese Academy of Sciences, Chinese Academy of Sciences , Lanzhou 73000 , China.
Journal of the American Chemical Society
|March 12, 2019
Resumen
Este estudio introduce un nuevo método catalizado por iridio para la berilización asimétrica de C-H, creando ácidos organobóricos ópticamente activos. Los nuevos ligandos quirales permiten una síntesis eficiente de valiosos compuestos borilados de aminas.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Química medicinal
Sus antecedentes:
- Los ácidos organobóricos ópticamente activos son cruciales en varios campos químicos.
- La síntesis catalítica asimétrica de estos compuestos sigue siendo un desafío, especialmente utilizando métodos atómicos y económicos.
Objetivo del estudio:
- Desarrollar un nuevo y eficiente método catalítico asimétrico para la síntesis de ácidos organoborónicos ópticamente activos.
- Informar sobre una borilación asimétrica de enlaces aromáticos C-H catalizada por el iridio y dirigida por quelantes.
Principales métodos:
- Se utilizó una nueva familia de ligandos borílicos bidentados quirales (L) derivados de la (S,S) -1,2-difenil-1,2-etanediamina ((S,S) -DPEN).
- Se ha empleado la catálisis del iridio para la borilación asimétrica C ((sp2) -H, incluida la desimetrización de las diarilmetilaminas procirales y la resolución cinética de las diarilmetilaminas racémicas.
- Se realizaron cálculos DFT para elucidar las vías de reacción.
Principales resultados:
- Se logró una alta regioselectividad y buenas a excelentes enantioselectividades (hasta el 96% ee) en la desimetrización de 26 ejemplares de diarilmetilaminas procirales.
- Se obtuvieron buenos valores de selectividad (hasta el 68%) en la resolución cinética de 11 ejemplos de diarilmetilaminas racémicas.
- Utilidad sintética demostrada a escala de gramos y conversión de enlaces C-B en diversas funcionalidades (C-O, C-C, C-Br, C-P).
Conclusiones:
- Desarrolló un método de borilación asimétrico catalizado por iridio versátil y eficiente.
- Los nuevos ligandos quirales de boro son clave para lograr una alta estereoselectividad en la síntesis de valiosos derivados del ácido organoborónico.
- La metodología ofrece una vía práctica para acceder a compuestos ópticamente activos con amplias aplicaciones sintéticas.
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