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Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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Friedel–Crafts reactions were developed in 1877 by the French chemist Charles Friedel and the American chemist James Crafts. Friedel–Crafts alkylation refers to the replacement of an aromatic proton with an alkyl group via electrophilic aromatic substitution. A Lewis acid catalyst such as aluminum chloride reacts with an alkyl halide to form a carbocation. The resulting carbocation then reacts with the aromatic ring and undergoes a series of electron rearrangements before giving the final...

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La fluoración de C-H aliloide catalizada por el paladio con fluoración de C-H.

Marie-Gabrielle Braun1, Abigail G Doyle

  • 1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.

Journal of the American Chemical Society
|August 17, 2013
PubMed
Resumen

Este estudio introduce la primera fluoración catalítica de C-H alílico utilizando fluoruro nucleófilo. El nuevo sistema de cocatalizador de paladio/cromo produce eficientemente fluoruros alelicos con excelente regioselectividad bajo condiciones suaves.

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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • Química organometálica Química orgánica de los metales.
  • Fluoración Química de la fluoración

Sus antecedentes:

  • Los fluoruros alílicos son valiosos intermediarios sintéticos.
  • Los métodos existentes para la fluoración alilica a menudo requieren sustratos prefuncionalizados o condiciones duras.
  • El desarrollo de métodos de funcionalización directa de C-H es un objetivo clave en la química sintética.

Objetivo del estudio:

  • Para reportar la primera reacción catalítica directa de fluoración de C-H.
  • Desarrollar un método que utilice una fuente de fluoruro nucleofílico.
  • Establecer un protocolo suave y regioselectivo para la síntesis de fluoruros alílicos.

Principales métodos:

  • Utilizó un sistema de cocatalizador de paladio (Pd) y cromo (Cr).
  • Utilizó trietilamina trihidrofluoruro (Et3N·3HF) como fuente de fluoruro nucleófilo.
  • Investigó la reacción con sustratos simples de olefinas.

Principales resultados:

  • Logró la primera fluoración catalítica directa de C-H alilico con un fluoruro nucleófilo.
  • Se obtienen buenos rendimientos de fluoruros alílicos.
  • Se ha demostrado una alta regioselectividad ramificada a lineal en los productos de fluoración.
  • La reacción se produce en condiciones suaves.

Conclusiones:

  • La reacción catalizada Pd/Cr desarrollada ofrece una nueva y poderosa ruta hacia los fluoruros alílicos.
  • Este método proporciona una alternativa a los enfoques tradicionales que requieren materiales de partida prefuncionalizados.
  • El amplio alcance y las condiciones suaves mejoran su utilidad en la síntesis orgánica.