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Organoborano catalizado regioselectivo 1,4-hidroboración de las piridinas

Xiaoting Fan¹, Junhao Zheng¹, Zhen Hua Li¹

¹Collaborative Innovation Center of Chemistry for Energy Material, Shanghai Key Laboratory of Molecular Catalysis and Innovative Material, Department of Chemistry, Fudan University, Handan Road 220, Shanghai, 200433, China.

Journal of the American Chemical Society

|April 8, 2015

Resumen

Un nuevo y voluminoso organoborano actúa como catalizador para la hidroboración de las piridinas. Esta reacción frustrada de la pareja de Lewis es altamente selectiva y se produce en condiciones suaves.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
La catálisis por catálisis.
Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

Los pares de Lewis frustrados (FLP) son ácidos y bases de Lewis que no pueden formar aductos clásicos.
Los FLPs son conocidos por su capacidad para activar moléculas pequeñas.
Los organoboranos son reactivos versátiles en la síntesis orgánica.

Objetivo del estudio:

Para sintetizar un organoborano voluminoso, Ar (((F) 2BMe (1). para sintetizar un organoborano muy voluminoso, Ar (((F) 2BMe (1). para sintetizar un organoborano muy voluminoso, Ar (((F) 2BMe (1). para sintetizar un organoborano muy voluminoso, Ar (((F) 2BMe (1). para sintetizar un organoborano muy voluminoso.
Para investigar la actividad catalítica del organoborano 1 con la piridina.
Para explorar la 1,4-hidroboración de las piridinas utilizando la química frustrada del par de Lewis.

Principales métodos:

Síntesis de un organoborano voluminoso llamado Ar(F) 2BMe.
Formación de un par de Lewis frustrado entre el organoborano y la piridina en solución.
1,4-hidroboración catalítica de piridinas bajo condiciones suaves.
Caracterización de los intermediarios de reacción utilizando espectroscopia de RMN y cálculos DFT.

Principales resultados:

Se sintetizó con éxito el voluminoso organoborano Ar(F) 2BMe (1).
El organoborano 1 y la piridina formaron un par de Lewis frustrado en la solución C6D6.
El Compuesto 1 catalizó eficientemente la 1,4-hidroboración de varias piridinas.
La reacción exhibió una alta quimio y regioselectividad.
Se identificó y caracterizó un intermediario del complejo de boronio, [Py2Bpin][Ar(F) 2B(H) Me] (3), fue identificado y caracterizado.

Conclusiones:

Un nuevo y voluminoso organoborano permite la catálisis frustrada del par de Lewis para la hidroboración de piridina.
El método desarrollado ofrece una ruta altamente selectiva y eficiente para la funcionalización de la piridina.
El estudio proporciona información sobre el mecanismo de la hidroboración catalizada por FLP a través de la caracterización intermedia.

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