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Tris ((bicyclo[1.1.1]pentyl) phosphine: Un Tri-tert-alkylphosphine excepcionalmente pequeño y su complejo Pd ((0)

Griffin L Perry¹, Nathan D Schley¹

¹Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, United States.

Journal of the American Chemical Society

|March 15, 2023

Resumen

Los investigadores sintetizaron la tri-ter-alquilfosfina más pequeña, la tris ((biciclo[1.1.1]) pentilfosfina (PBcp3), a través de la adición de radicales. Este nuevo ligando de fosfina permite complejos de paladio altamente reactivos para reacciones de acoplamiento cruzado que involucran haluros de alquilo.

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Área de la Ciencia:

Química organometálica
Química sintética
Catálisis

Sus antecedentes:

Las tri-ter-alquilfosfinas son ligandos cruciales en la catálisis.
El desarrollo de ligandos de fosfina estéricamente exigentes es un desafío continuo.
Las fosfinas pequeñas y ricas en electrones pueden ofrecer una reactividad única.

Objetivo del estudio:

Para sintetizar y caracterizar una nueva, estéricamente pequeña tri-tert-alquilfosfina.
Evaluar las propiedades electrónicas y estéricas de la nueva fosfina.
Para explorar su utilidad como ligando en reacciones de acoplamiento cruzado catalizadas por paladio.

Principales métodos:

Adición radical de fosfina (PH3) al propeleno.
Síntesis de tris ((biciclo[1.1.1]pentilo) fosfina (PBcp3) y PBcp2Ph.
Formación y caracterización de un complejo de paladio biligado, Pd, PBcp3.
Prueba de la actividad catalítica en el acoplamiento cruzado de electrófilos sp3.

Principales resultados:

Con éxito sintetizó PBcp3, la tri-ter-alquilfosfina más pequeña conocida.
PBcp3 presenta un volumen estérico comparable al de la trietilfosfina (PEt3), pero es más pequeño que el de la triciclohexilfosfina (PCy3).
Pd(PBcp3) 2 demuestra una reactividad excepcional en adición oxidativa con haluros de alquilo y es eficaz en reacciones de acoplamiento cruzado.

Conclusiones:

La adición radical al [1.1.1]propelano es una vía viable para los nuevos ligandos de la biciclopentilofosfina.
PBcp3 es un ligando altamente efectivo para el acoplamiento cruzado catalizado por paladio de electrófilos sp3 desafiantes.
Este trabajo amplía el alcance de los ligandos de fosfina para aplicaciones catalíticas avanzadas.