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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

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Datos La carbonilación aril-enantioselectiva catalizada por el paladio de las sulfonimidamidas habilitada por la

Lucy van Dijk¹, Brittany C Haas¹, Ngiap-Kie Lim²

¹Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, United States.

Journal of the American Chemical Society

|September 1, 2023

Resumen

Un nuevo método catalizado por el paladio permite la síntesis asimétrica de sulfonimidamidas. Optimización guiada por la ciencia de los datos para una carbonilación de arilo eficiente y enantioselectiva, avanzando en el descubrimiento medicinal y agroquímico.

Área de la Ciencia:

Química orgánica
Catálisis
Química medicinal

Sus antecedentes:

Las sulfonimidamidas son bloques de construcción cruciales en la química medicinal y el descubrimiento agroquímico.
Es muy deseable desarrollar métodos de síntesis asimétricos generales para las sulfonimidamidas.

Objetivo del estudio:

Informar sobre un nuevo método de acoplamiento cruzado catalizado por el paladio para la carbonilación arilo enantioselectiva de las sulfonimidamidas.
Utilizar técnicas de ciencia de datos para la optimización de la reacción y la exploración del alcance.

Principales métodos:

Utilizando la catálisis del paladio para la carbonilación asimétrica del arilo.
Utilización de la ciencia de datos, incluidas las bibliotecas de ligandos virtuales y el análisis de descriptores, para optimizar las condiciones de reacción.
Explorando sistemáticamente el alcance con varios yoduros de arilo y heteroarilo y sulfonimidamidas racémicas.

Principales resultados:

Se obtiene un excelente rendimiento y enantioselectividad en la síntesis de sulfonimidamidas.
Ha aplicado con éxito estrategias basadas en la ciencia de los datos para orientar la optimización de los catalizadores y las reacciones.
Determinación del alcance y las limitaciones del método desarrollado mediante pruebas de diversos sustratos.

Conclusiones:

El método desarrollado proporciona una vía general y eficiente para obtener sulfonimidamidas enriquecidas con enantio.
La integración de la ciencia de datos aceleró significativamente la optimización de la reacción y la evaluación del alcance.
Este enfoque facilita la aplicación de las sulfonimidamidas en la investigación industrial y académica.

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