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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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Published on: April 1, 2013

La fluorosulfonilación intermolecular altamente selectiva Pd-catalizada de los estirenos es una fluorosulfonilación

Zheliang Yuan¹, Hao-Yang Wang, Xin Mu

¹State Key Laboratory of Organometallic Chemistry and ‡National Center for Organic Mass Spectrometry in Shanghai, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai, China , 200032.

Journal of the American Chemical Society

|February 5, 2015

Resumen

Una nueva reacción catalizada por el paladio permite la fluorosulfonilación selectiva de estirenos, creando valiosos beta-fluoro sulfonos. Este método ofrece una amplia tolerancia de grupo funcional y procede a través de un mecanismo inusual que involucra a una especie de paladio de alta valencia.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis es la catálisis.
Química del Fluororgánico Química del Fluororgánico

Sus antecedentes:

Las reacciones catalizadas por el paladio son cruciales en la síntesis orgánica moderna.
El desarrollo de métodos selectivos para la introducción de fluoro y grupos sulfonilo es de gran interés.
Los métodos de fluoración anteriores a menudo carecen de control sobre la región y la estereoquímica.

Objetivo del estudio:

Desarrollar un nuevo método catalizado por paladio para la síntesis de beta-fluoro sulfonas.
Para lograr la fluorosulfonilación regioselectiva y diastereoselectiva de estirenos.
Para explorar el mecanismo de reacción y la tolerancia del grupo funcional.

Principales métodos:

Utilizó una nueva reacción intermolecular catalizada por Pd.
Empleó condiciones de reacción suaves.
Se ha investigado la tolerancia del grupo funcional con varios estirenos y ácidos arilsulfínicos.

Principales resultados:

Sintetizó con éxito varios beta-fluoro sulfonos con alta regio- y diastereoselectividad.
Se ha demostrado una amplia tolerancia del grupo funcional tanto para los estirenos como para los ácidos arilsulfínicos.
Un estudio mecanicista preliminar sugirió una vía inusual que involucra una especie de L2Pd (III) F de alta valencia y un radical de carbono bencílico.

Conclusiones:

Desarrolló una nueva y eficiente fluorosulfonilación catalizada por Pd de estirenos.
La reacción ofrece una nueva ruta a las beta-fluorosulfonas con excelente selectividad.
El mecanismo propuesto proporciona nuevos conocimientos sobre la formación de enlaces C-F mediados por el paladio.

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