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Hidratación de alquinas terminales catalizadas por complejos de porfirina de cobalto solubles en agua

Tadashi Tachinami¹, Takuho Nishimura, Richiro Ushimaru

¹Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan.

Journal of the American Chemical Society

|December 20, 2012

Resumen

Los catalizadores de porfirina de cobalto soluble en agua (III) convierten eficientemente las alquinas terminales en cetonas de metilo. Esta reacción de hidratación es compatible con diversos grupos funcionales y se puede realizar en una escala de gramos con recuperación del catalizador.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Química verde es la química verde.

Sus antecedentes:

Las alquinas terminales son versátiles bloques de construcción en la síntesis orgánica.
Los métodos eficientes y selectivos para la hidratación de alquinos a metilcetonas son cruciales.
Los métodos existentes a menudo requieren condiciones duras o carecen de tolerancia al grupo funcional.

Objetivo del estudio:

Desarrollar un nuevo sistema catalítico para la hidratación de alquinas terminales.
Para lograr altos rendimientos y selectividad en la formación de metilcetona.
Demostrar la compatibilidad del sistema catalítico con varios grupos funcionales sensibles.

Principales métodos:

Utilizó complejos de porfirina de cobalto soluble en agua (III) como catalizadores.
Investigó la hidratación de diversos sustratos alquinos terminales.
Condiciones de reacción optimizadas, incluida la carga del catalizador (0.12 mol %).

Principales resultados:

Se obtienen buenos a excelentes rendimientos para la hidratación de alquinas terminales a metilcetonas.
Se ha demostrado una amplia tolerancia al grupo funcional, incluidos los grupos sensibles al ácido/base y los grupos sensibles al redox.
Realizó con éxito la reacción en una escala de gramos con una recuperación directa del catalizador a través del procesamiento acuoso.

Conclusiones:

Los complejos de porfirina de cobalto soluble en agua representan un catalizador eficaz para la hidratación de alquinos.
El método desarrollado ofrece una ruta ecológica y eficiente a las metilcetonas desde sustratos alquinos difíciles.
La robustez del catalizador y la facilidad de recuperación lo hacen adecuado para aplicaciones prácticas.

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