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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

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Regioselectividad Aromática Perfluoro-tert-butilación Utilizando Perfluoro-tert-butilo Fenil Sulfona y Arinas

Zhiqiang Wei^1,2, Lixian Wen¹, Kaidi Zhu^1,2

¹Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032, China.

Journal of the American Chemical Society

|December 7, 2022

Resumen

Los investigadores desarrollaron un nuevo método para la butilación de perfluoro-tercio aromático utilizando una nueva fuente de aniones PFtB. Este avance permite una síntesis eficiente de arenas perfluoro-tert-butiladas y sondas avanzadas de RMN.

Área de la Ciencia:

Química orgánica
Química del fluor
Metodología sintética

Sus antecedentes:

La introducción del grupo perfluoro-tert-butilo (PFtB) en las arenas es un desafío.
El grupo PFtB es un análogo más voluminoso del grupo CF3, que ofrece propiedades únicas.

Objetivo del estudio:

Establecer el primer protocolo sintético general para la butilación de perfluoro-tercio aromático.
Desarrollar un método fiable para incorporar el grupo PFtB en compuestos aromáticos.

Principales métodos:

Identificación de la perfluoro-tert-butilfenil sulfona como una nueva fuente de aniones PFtB.
Reacción del anión PFtB con las arinas con alta regioselectividad.

Principales resultados:

Síntesis exitosa de arenos butilados de perfluoro-tercio en altos rendimientos.
Demostración de la utilidad del método en la preparación de sondas RMN sensibles etiquetadas con 19F.

Conclusiones:

El protocolo desarrollado proporciona una solución general para la butilación con perfluoro-tercio aromático.
El nuevo método facilita la creación de sondas de RMN con capacidades de resolución excepcionales.

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