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1,1-Difuncionalización selectiva del sitio de alquenos no activados habilitada por catálisis de paladio catiónico

Jinwon Jeon^1,2, Ho Ryu^1,2, Changseok Lee^1,2

¹Department of Chemistry , Korea Advanced Institute of Science and Technology (KAIST) , Daejeon , 34141 , Korea.

Journal of the American Chemical Society

|June 1, 2019

Resumen

Una nueva reacción catalizada por el paladio permite la 1,1-difuncionalización de alquenos utilizando dos nucleófilos. Este método crea eficientemente moléculas complejas, incluidas aquellas con centros de carbono oxocuaternarios, con un alto control regional.

Área de la Ciencia:

Química orgánica
Catálisis
Química sintética

Sus antecedentes:

La catálisis del paladio es crucial para la formación de enlaces C-C.
La 1,1-difuncionalización de alquenos sigue siendo un desafío sintético.
Es importante desarrollar métodos regioselectivos para la funcionalización de alceno.

Objetivo del estudio:

Desarrollar una nueva disfuncionalización catalizada por el paladio (II) de alquenos.
Para utilizar un complejo catiónico de paladio para la difuncionalización de alquenos.
Investigar el mecanismo de la reacción a través de experimentos y cálculos DFT.

Principales métodos:

Catalización con un complejo catiónico de paladio.
Adición regioselectiva de nucleófilos a los alquenos.
Formación de un intermediario clave de η3-π-allilo de paladio.
Optimización de la reacción para varios sustratos.

Principales resultados:

El éxito de la 1,1-difuncionalización de alquenos terminales y internos no activados.
Síntesis de productos γ,γ- o δ,δ-difuncionalizados a partir de indolos/anilinas y alquenos.
Permitiendo la desfuncionalización asimétrica 1,1- para formar centros de carbono oxocuaternario.
Se ha logrado un alto control regional en todas las transformaciones.

Conclusiones:

Se ha establecido un método versátil catalizado por el paladio para la desfuncionalización del alqueno 1,1.
La reacción proporciona acceso a valiosos compuestos difuncionalizados y arquitecturas moleculares complejas.
Los conocimientos mecanicistas ayudan en el desarrollo de las transformaciones catalizadas por el paladio.

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