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Updated: Aug 30, 2025

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Difuncionalización iodinativa intermolecular asimétrica de las sulfonamidas alilicas habilitada por catálisis de

Lihao Liao¹, Xinru Xu¹, Jieying Ji¹

¹Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry, Sun Yat-Sen University, Guangzhou 510006, P. R. China.

Journal of the American Chemical Society

|September 2, 2022

Resumen

Este estudio introduce un nuevo catalizador de sulfuro quiral para la difuncionalización iodinativa asimétrica de alquenos. Este método crea eficientemente valiosas moléculas quirales que contienen yodo a partir de sustratos difíciles, ofreciendo una nueva vía sintética.

Área de la Ciencia:

Química orgánica
Catálisis asimétrica
Metodología sintética

Sus antecedentes:

La halogenación electrofílica de alquenos es crucial para la síntesis de moléculas funcionalizadas.
La difuncionalización intermolecular asimétrica catalítica de los alquenos presenta desafíos sintéticos significativos.

Objetivo del estudio:

Desarrollar una difuncionalización iodinativa intermolecular catalítica asimétrica eficiente de los alquenos.
Para utilizar un catalizador de sulfuro quiral básico de Lewis para esta transformación.

Principales métodos:

Empleo de un catalizador de sulfuro quiral básico de Lewis para la difuncionalización iodinativa electrófila.
Utilizando sustratos desafiantes como las sulfonamidas alilicas γ,γ-disubstituidas y los alquenos 1,1-disubstituidos.
Incorpora varios nucleófilos, incluidos los fenoles, los alcoholes, el fluoruro y la azida.

Principales resultados:

Se ha logrado una síntesis eficiente de moléculas quirales funcionalizadas con yodo con excelentes enantio- y diastereoselectividades.
Se ha demostrado la incorporación exitosa de diversos nucleófilos.
Mostró la versatilidad de los productos yodados como moléculas de plataforma para futuras transformaciones.

Conclusiones:

El enfoque desarrollado catalizado por sulfuro quiral proporciona una solución efectiva para la difuncionalización iodinativa asimétrica.
El catalizador permite la construcción enantioselectiva de iones quirales de yodo.
Los productos resultantes sirven como valiosos precursores para diversos compuestos quirales.

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