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Videos de Conceptos Relacionados

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
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.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.8K
Introduction
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.
7.8K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.4K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.4K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

10.3K
Introduction
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.
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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.2K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
8.2K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

9.9K

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Catalización asimétrica anti-Selectiva de las borilaquinas terminales por el níquel

Chengmi Huang1, Dong Wu1, Yangyang Li1

  • 1The Institute for Advanced Studies, Wuhan University, Wuhan, Hubei 430072, People's Republic of China.

Journal of the American Chemical Society
|August 15, 2023
PubMed
Resumen

Este estudio introduce una nueva reacción catalizada por níquel para crear alquenos sustituidos a partir de alquinas. El método logra una alta selectividad en un acoplamiento de tres componentes, ofreciendo una ruta práctica a valiosos compuestos enantioenriquecidos.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Síntesis asimétrica

Sus antecedentes:

  • La transformación selectiva de alquinas en alquenos es crucial para la síntesis de alquenos sustituidos.
  • Lograr reacciones enantioselectivas multicomponentes con alta selectividad sigue siendo un desafío significativo en la síntesis orgánica.

Objetivo del estudio:

  • Desarrollar una borilcarbofuncionalización antistereoselectiva asimétrica sin precedentes de las alquinas terminales.
  • Establecer una reacción de acoplamiento cruzado de tres componentes eficiente utilizando la catálisis del níquel.

Principales métodos:

  • Acoplamiento cruzado de tres componentes catalizado por níquel de alquinas terminales, un reactivo de diboro y electrofilos alquilo procirales.
  • Utilizó un ligando de diamina quiral barato para controlar la selectividad.

Principales resultados:

  • Se obtienen elevadas regioselectividades, estereoselectividades y enantioselectividades en la reacción de borilcarbofuncionalización.
  • Desarrolló un protocolo eficiente para acceder a ésteres alqueniles enriquecidos con enantio con un centro α-esterogénico.
  • Demostrado amplio alcance y excelente compatibilidad de grupo funcional.

Conclusiones:

  • El método desarrollado proporciona un enfoque práctico y versátil para sintetizar moléculas complejas.
  • La reacción es valiosa para las derivaciones estereorretentivas y la síntesis de moléculas de fármacos.