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El acoplamiento migratorio de radicales catalizados por níquel permite la arilación C-2 de los carbohidratos
Gaoyuan Zhao1, Wang Yao1, Ilia Kevlishvili2
1Department of Chemistry, State University of New York, Stony Brook, New York 11794, United States.
Journal of the American Chemical Society
|June 4, 2021
Resumen
Este estudio introduce la primera reacción catalizada por níquel para sintetizar 2-arilo-2-deoxiglicosidos. Este nuevo método crea de manera eficiente imitaciones complejas de carbohidratos a partir de materiales iniciales simples utilizando el acoplamiento cruzado migratorio radical.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Química de los carbohidratos
Sus antecedentes:
- La catálisis del níquel es una herramienta poderosa para la síntesis orgánica.
- El desarrollo de nuevos métodos para la modificación de carbohidratos es crucial.
Objetivo del estudio:
- Para reportar la primera reacción de acoplamiento cruzado de radicales migratorios catalizados por níquel.
- Para sintetizar 2-arilo-2-deoxiglicosidos directamente a partir de 1-azúcares y ácidos arilborónicos.
Principales métodos:
- Utilizando la catálisis de níquel para el acoplamiento cruzado migratorio radical.
- Utilizando azúcares 1-bromos y ácidos arilborónicos como materias primas.
- Investigar los mecanismos de reacción a través de estudios experimentales y computacionales.
Principales resultados:
- Síntesis exitosa de 2-arilo-2-deoxiglicósidos.
- Demostrado amplio alcance de sustrato y tolerancia de grupo funcional.
- Propuso un mecanismo de reacción que involucra una reorganización concertada de 1,2-aciloxi y la formación de enlaces C-C.
Conclusiones:
- La nueva reacción catalizada por níquel proporciona una ruta eficiente para los mimos de carbohidratos arilados C-2.
- Este método expande la utilidad de la catálisis del níquel en la síntesis orgánica.
- Permite nuevas desconexiones de enlaces estratégicos en la química de los carbohidratos.
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