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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

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Dicarbofuncionalización catalizada por cobre de las olefinas no activadas por ciclización en tándem/acoplamiento

Surendra Thapa¹, Prakash Basnet¹, Ramesh Giri¹

¹Department of Chemistry & Chemical Biology, The University of New Mexico , Albuquerque, New Mexico 87131, United States.

Journal of the American Chemical Society

|April 14, 2017

Resumen

Este estudio introduce un nuevo método para la difuncionalización de las olefinas, lo que permite la síntesis de carbo y heterociclos complejos. El enfoque crea eficientemente enlaces carbono-carbono utilizando la ciclización radical y la catálisis del cobre.

Área de la Ciencia:

Química orgánica
Metodología sintética
Catálisis

Sus antecedentes:

La disfuncionalización de las olefinas no activadas sigue siendo un desafío importante en la síntesis orgánica.
El desarrollo de métodos eficientes para construir andamios carbocíclicos y heterocíclicos complejos es crucial para el descubrimiento de fármacos y la ciencia de los materiales.

Objetivo del estudio:

Presentar una nueva estrategia para la desfuncionalización de las olefinas no activadas.
Para sintetizar diversos carbo- y heterociclos (N, O) utilizando materiales de partida fácilmente disponibles.

Principales métodos:

Utiliza reactivos alquilo/arilzinco derivados de haluros alquilo/arilo atados a las olefinas.
Utiliza la ciclización radical para generar complejos intermedios C ((sp3) -Cu in situ.
Interceptación de los complejos de cobre con ioduros de arilo y heteroarilo.

Principales resultados:

Difuncionalizó exitosamente las olefinas no activadas en las posiciones 1,2 con dos entidades basadas en carbono.
Demostró la síntesis de una variedad de carbo y heterociclos (arilmetilo).
Estableció una nueva ruta para la construcción de estructuras cíclicas complejas.

Conclusiones:

El método presentado ofrece un enfoque versátil y eficiente para la difuncionalización de la olefina.
Esta estrategia proporciona acceso a valiosos compuestos carbocíclicos y heterocíclicos.
La generación in situ y la interceptación de complejos C ((sp3) -Cu representan una poderosa herramienta sintética.

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