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La olefinación catalizada por Pd (II) de los enlaces C-H de sp3

Masayuki Wasa¹, Keary M Engle, Jin-Quan Yu

¹Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Journal of the American Chemical Society

|March 2, 2010

Resumen

Una nueva reacción catalizada por el paladio permite la olefinación de sp3 C-H utilizando grupos de dirección de N-arilamida. Este método produce eficientemente gamma-lactamas y es eficaz para sustratos de ciclopropano.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Metodología sintética de la metodología sintética.

Sus antecedentes:

La funcionalización C-H catalizada por el paladio es una herramienta poderosa en la síntesis orgánica.
El desarrollo de nuevas reacciones de olefinación C-H sigue siendo un desafío significativo.

Objetivo del estudio:

Desarrollar la primera reacción de olefinación C-H catalizada por el paladio (II) -sp3.
Explorar la utilidad de los grupos de dirección de N-arilamida en esta transformación.

Principales métodos:

Utilizado en la catálisis del paladio (II) con grupos de dirección de N-arilamida.
Investigó el alcance de la reacción y la compatibilidad del sustrato.
Analizó la formación de los intermediarios gamma-lactámicos.

Principales resultados:

Se logró con éxito la primera olefinación sp3 C-H catalizada por PdII.
La reacción procedió de manera eficiente con varios sustratos, incluidos los con átomos de hidrógeno alfa.
Productos gamma-lactámicos generados a través de la adición subsecuente de 1,4.
Aplicabilidad demostrada para la olefinación de metileno C-H de sustratos de ciclopropano.

Conclusiones:

Estableció un método nuevo y eficiente para la olefinación sp3 C-H.
La metodología desarrollada ofrece una nueva ruta a los gamma-lactamas.
Destaca la versatilidad de los grupos de dirección de N-arilamida en la activación de C-H.

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