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Preparation of Alkynes: Alkylation Reaction02:27

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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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Preparation of Alkynes: Dehydrohalogenation02:34

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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.
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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.
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Electrophilic Addition to Alkynes: Halogenation02:38

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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.
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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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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...
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Xantilación C-H: una plataforma sintética para la funcionalización de alcano

William L Czaplyski1, Christina G Na1, Erik J Alexanian1

  • 1Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States.

Journal of the American Chemical Society
|October 15, 2016
PubMed
Resumen

Este estudio introduce un nuevo método de funcionalización de C-H utilizando N-xantilamida y LED azules. Este avance expande las estructuras químicas accesibles para la síntesis de moléculas complejas y la derivación en etapa tardía.

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Área de la Ciencia:

  • Química orgánica
  • Química sintética
  • Catálisis

Sus antecedentes:

  • La funcionalización intermolecular de los enlaces alifáticos C-H es crucial para la síntesis de moléculas complejas.
  • Los métodos actuales de funcionalización C-H tienen limitaciones en el espacio químico accesible.

Objetivo del estudio:

  • Desarrollar un nuevo método de funcionalización C-H que amplíe el rango de quimiotipos accesibles.
  • Para permitir una derivatización eficiente en etapa tardía de moléculas complejas.

Principales métodos:

  • Utilizando diodos emisores de luz azul (LED) para la xantilación de C-H.
  • Utilizando una N-xantilamida fácilmente preparada como reactivo clave.
  • Investigación de la reacción en condiciones en las que el sustrato es el reactivo limitante.

Principales resultados:

  • Se obtienen rendimientos químicos útiles para la xantilación C-H.
  • Se ha demostrado una alta selectividad del sitio en las funcionalizaciones de fase tardía de moléculas complejas.
  • Muestra tolerancia de una variedad de grupos funcionales comunes dentro de la reacción.

Conclusiones:

  • El método de xantilación de C-H desarrollado amplía significativamente el alcance de las transformaciones de C-H accesibles.
  • La versatilidad del grupo funcional xantato se aprovecha a través de vías polares y radicales.
  • Este enfoque abre rutas sintéticas previamente inaccesibles para moléculas complejas.