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Videos de Conceptos Relacionados

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Ethers to Alkyl Halides: Acidic Cleavage02:18

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Ethers are generally unreactive and unsuitable for direct nucleophilic substitution reactions since the alkoxy groups are strong bases and, therefore, poor leaving groups. However, ethers readily undergo acidic-cleavage reactions. Ethers can be converted to alkyl halides when heated with strong acids such as HBr and HI in a sequence of two substitution reactions.
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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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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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Escisión quimioselectiva de enlaces de Si-C en tetraalquilosilanos no activados mediante el uso de trifluoroacetato

Keitaro Matsuoka1, Narumi Komami1, Masahiro Kojima1

  • 1Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.

Journal of the American Chemical Society
|December 28, 2020
PubMed
Resumen
Este resumen es generado por máquina.

Los investigadores desarrollaron un nuevo método para romper los enlaces silicio-carbono en tetraalquilosilanos simples utilizando tris (trifluoroacetato) de yodo. Este avance permite el uso de estos compuestos estables como precursores versátiles en la síntesis orgánica.

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Área de la Ciencia:

  • Química orgánica
  • Química del silicio orgánico
  • Desarrollo de la metodología sintética

Sus antecedentes:

  • Los enlaces de silicio-carbono (Si-Csp3) no activados en tetraalquilosilanos son típicamente inertes bajo condiciones de reacción estándar.
  • Esta inercia limita la utilidad sintética de los tetraalquilosilanos simples como precursores en la síntesis orgánica.
  • El desarrollo de métodos para la escisión selectiva de enlaces Si-Csp3 es crucial para ampliar su aplicación.

Objetivo del estudio:

  • Informar sobre un nuevo método quimioselectivo para la escisión de enlaces Si-Csp3 en tetraalquilosilanos no activados.
  • Demostrar la utilidad de este método para permitir transformaciones posteriores, como la oxidación de Tamao-Fleming.
  • Proporcionar una estrategia de precursores sintéticos estables mediante el uso de tetraalquilosilanos fácilmente disponibles.

Principales métodos:

  • Clivado quimioselectivo de los enlaces Si-Csp3 mediante el uso de trifluoroacetato de yodo.
  • Optimización de la reacción en condiciones suaves (por ejemplo, -50 °C a temperatura ambiente).
  • Investigación mecanicista mediante espectroscopia de resonancia magnética nuclear (RMN) y cálculos de la teoría funcional de la densidad (TFD).

Principales resultados:

  • Se logró una escisión quimioselectiva exitosa de los enlaces Si-Csp3 en tetraalquilosilanos no activados.
  • La reacción se desarrolla sin problemas en condiciones suaves y tolera varios grupos funcionales polares.
  • La subsiguiente oxidación Tamao-Fleming proporciona acceso a los alcoholes correspondientes.
  • Los estudios mecánicos sugieren una transferencia concertada de grupos alquilo del silicio al yodo y la formación de enlaces Si-O.

Conclusiones:

  • Se ha establecido una nueva vía sintética para activar los tetraalquilosilanos no activados.
  • Este método proporciona una herramienta valiosa para la incorporación de tetraalquilosilanos en estrategias sintéticas.
  • El protocolo desarrollado ofrece un enfoque de precursor estable y versátil para la síntesis orgánica.