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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

Dihidrofuncionalización diferencial de alquinas terminales: síntesis de alquilboronatos bencílicos a través del

Megan K Armstrong¹, Gojko Lalic¹

¹Department of Chemistry , University of Washington , Seattle , Washington 98195 , United States.

Journal of the American Chemical Society

|April 4, 2019

Resumen

Este estudio introduce un nuevo método de acoplamiento reductivo para las alquinas terminales, los haluros de arilo y el pinacolborano. Este proceso logra la dihidrofuncionalización diferencial, produciendo valiosos productos de alquilborato bencílico.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Las alquinas terminales son bloques de construcción versátiles en la síntesis orgánica.
El desarrollo de métodos eficientes para la funcionalización de alquinas es crucial para crear moléculas complejas.
Los métodos existentes a menudo carecen de selectividad o requieren condiciones duras.

Objetivo del estudio:

Desarrollar un método novedoso, eficiente y selectivo para la dihidrofuncionalización diferencial de las alquinas terminales.
Establecer una reacción de acoplamiento de tres componentes para sintetizar productos de alquilboronato bencílico.
Para elucidar el mecanismo de reacción y explorar su alcance de sustrato.

Principales métodos:

Se utilizó un sistema catalítico cooperativo de cobre y paladio.
La reacción involucró el acoplamiento reductor de tres componentes de alquinas terminales, haluros de arilo y pinacolborano.
Se realizaron estudios mecánicos, incluidos experimentos cinéticos.

Principales resultados:

Se logró con éxito la dihidrofuncionalización diferencial de las alquinas terminales.
La reacción demostró un excelente alcance del sustrato, tolerando varios grupos funcionales.
Los productos de alquilboronato bencílico se sintetizaron con una alta eficiencia.

Conclusiones:

Se ha desarrollado una nueva y eficiente reacción de acoplamiento reductivo para las alquinas terminales.
La catálisis cooperativa de cobre y paladio permite la difuncionalización selectiva.
Este método proporciona una vía valiosa para los boronatos alquilo bencílicos.

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