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Formación de enlaces decarboxilativos organofotoredóxicos
Shotaro Shibutani1, Taiga Kodo1, Mitsutaka Takeda1
1Division of Pharmaceutical Sciences, Graduate School of Medical Sciences , Kanazawa University , Kakuma-machi, Kanazawa 920-1192 , Japan.
Journal of the American Chemical Society
|January 4, 2020
Resumen
Este estudio introduce la catálisis de organosulfuro con luz visible para el acoplamiento descarboxilativo. Crea eficientemente enlaces C ((sp3) -O ((sp3)) a partir de alcoholes y derivados de ácido carboxílico utilizando ésteres redox activos.
Área de la Ciencia:
- Química orgánica
- Catálisis
- La fotoquímica
Sus antecedentes:
- Las reacciones de acoplamiento descarboxilativo son cruciales para la formación de enlaces C-C y C-heteroátomo.
- El desarrollo de sistemas catalíticos eficientes para la construcción de fragmentos C-O-C sigue siendo un desafío.
Objetivo del estudio:
- Informar de una nueva reacción de acoplamiento descarboxilativo catalizado por organosulfuro mediado por luz visible.
- Para permitir la formación de enlaces C ((sp3) -O ((sp3)) utilizando alcoholes alifáticos simples y ésteres redox activos derivados del ácido carboxílico.
Principales métodos:
- Catálisis fotorredóxica con luz visible utilizando un catalizador de organosulfuro.
- Utilizando ésteres redox activos derivados de ácido alquilo carboxílico terciario o secundario como socios de acoplamiento.
- Explorando la reactividad con varios nucleófilos heteroatómicos, incluidos los alcoholes, el agua, las amidas y los tiolos.
Principales resultados:
- Acoplamiento descarboxilativo exitoso entre alcoholes alifáticos simples y ésteres redox-activos para formar enlaces C ((sp3) -O ((C ((sp3).
- Demostración de la eficacia del sistema catalítico con diversos nucleófilos heteroatómicos.
- Establecimiento de una nueva ruta sintética para el éter y los compuestos relacionados.
Conclusiones:
- La catálisis de organosulfuro con luz visible proporciona un método eficaz para el acoplamiento descarboxilativo.
- La metodología desarrollada ofrece un enfoque versátil para la síntesis de fragmentos C(sp3) -O-C(sp3) y estructuras relacionadas.
- Este trabajo amplía el alcance de la catálisis fotorredóxica en la síntesis orgánica.
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