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Catalización del cobre para el heteroacoplamiento selectivo de alquinas terminales
Lebin Su1, Jianyu Dong1, Long Liu1
1State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University , Changsha 410082, China.
El heteroacoplamiento aeróbico catalizado por cobre de los alquinos terminales proporciona una nueva ruta a las 1,3-dinas asimétricas. Este método supera la preferencia tradicional por el homoacoplamiento en las reacciones de Glaser-Hay.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Metodología sintética
Sus antecedentes:
- La reacción de Glaser-Hay tradicionalmente favorece el homoacoplamiento de los alquinos terminales.
- La síntesis de 1,3-diinas asimétricas sigue siendo un desafío en la síntesis orgánica.
Objetivo del estudio:
- Desarrollar un nuevo método de heteroacoplamiento aeróbico catalizado por cobre.
- Para sintetizar una amplia gama de 1,3-diinas no simétricas.
Principales métodos:
- Utilizó un catalizador de cobre para el heteroacoplamiento aeróbico.
- Se emplean alquinas terminales como sustratos.
- Condiciones de reacción optimizadas para la formación selectiva de productos.
Principales resultados:
- Se ha logrado el heteroacoplamiento aeróbico selectivo de alquinas terminales.
- Sintetizó una amplia gama de 1,3-diinas asimétricas.
- Se obtienen buenos a excelentes rendimientos para los productos deseados.
Conclusiones:
- El método desarrollado permite una síntesis eficiente de 1,3-dinas asimétricas.
- Este trabajo desafía las reglas de selectividad establecidas de la reacción de Glaser-Hay.
- La catálisis del cobre ofrece una vía viable para el heteroacoplamiento selectivo de alquinos.
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02:27Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
02:40Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
02:38Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
02:34Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.