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Videos de Conceptos Relacionados

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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Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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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...
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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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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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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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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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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Difuncionalización iodinativa intermolecular asimétrica de las sulfonamidas alilicas habilitada por catálisis de

Lihao Liao1, Xinru Xu1, Jieying Ji1

  • 1Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry, Sun Yat-Sen University, Guangzhou 510006, P. R. China.

Journal of the American Chemical Society
|September 2, 2022
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio introduce un nuevo catalizador de sulfuro quiral para la difuncionalización iodinativa asimétrica de alquenos. Este método crea eficientemente valiosas moléculas quirales que contienen yodo a partir de sustratos difíciles, ofreciendo una nueva vía sintética.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis asimétrica
  • Metodología sintética

Sus antecedentes:

  • La halogenación electrofílica de alquenos es crucial para la síntesis de moléculas funcionalizadas.
  • La difuncionalización intermolecular asimétrica catalítica de los alquenos presenta desafíos sintéticos significativos.

Objetivo del estudio:

  • Desarrollar una difuncionalización iodinativa intermolecular catalítica asimétrica eficiente de los alquenos.
  • Para utilizar un catalizador de sulfuro quiral básico de Lewis para esta transformación.

Principales métodos:

  • Empleo de un catalizador de sulfuro quiral básico de Lewis para la difuncionalización iodinativa electrófila.
  • Utilizando sustratos desafiantes como las sulfonamidas alilicas γ,γ-disubstituidas y los alquenos 1,1-disubstituidos.
  • Incorpora varios nucleófilos, incluidos los fenoles, los alcoholes, el fluoruro y la azida.

Principales resultados:

  • Se ha logrado una síntesis eficiente de moléculas quirales funcionalizadas con yodo con excelentes enantio- y diastereoselectividades.
  • Se ha demostrado la incorporación exitosa de diversos nucleófilos.
  • Mostró la versatilidad de los productos yodados como moléculas de plataforma para futuras transformaciones.

Conclusiones:

  • El enfoque desarrollado catalizado por sulfuro quiral proporciona una solución efectiva para la difuncionalización iodinativa asimétrica.
  • El catalizador permite la construcción enantioselectiva de iones quirales de yodo.
  • Los productos resultantes sirven como valiosos precursores para diversos compuestos quirales.