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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
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Preparation and Reactions of Sulfides02:26

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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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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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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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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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α,β-Unsaturated carbonyl compounds with two electrophilic sites, the carbonyl carbon, and the β carbon, are susceptible to nucleophilic attack via two modes: conjugate or 1,4-addition and direct or 1,2-addition.
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Adición asimétrica de 2,3-sulfinilaminas con ácidos arilborónicos activada por la catálisis del níquel

Longlong Xi1, Xiaowu Fang1, Minyan Wang1

  • 1State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.

Journal of the American Chemical Society
|June 24, 2024
PubMed
Resumen
Este resumen es generado por máquina.

La síntesis de sulfinamidas quirales es un desafío. Este estudio introduce una adición de arilo asimétrico catalizado por níquel a las sulfinilaminas, creando diversas sulfinamidas S-quirogénicas con alta enantioselectividad.

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Área de la Ciencia:

  • Síntesis orgánica
  • Catálisis asimétrica
  • Química del organosulfuro

Sus antecedentes:

  • Las sulfinamidas son cruciales en la síntesis orgánica, con más de un siglo de investigación.
  • La creación eficiente de estereocentros en el átomo de azufre (centros S-quirogénicos) sigue siendo un obstáculo sintético significativo.

Objetivo del estudio:

  • Desarrollar un método versátil y eficaz para la síntesis de sulfinamidas S-quirogénicas.
  • Para lograr una alta enantioselectividad en la formación de estereocentros de azufre.

Principales métodos:

  • Adición catalítica asimétrica de arilo a las sulfinilaminas mediante el uso de un catalizador complejo de níquel.
  • Utilizó varios ácidos arilborónicos como agentes arilantes.
  • Incorpora estudios experimentales y computacionales detallados para comprender el mecanismo de reacción.

Principales resultados:

  • Con éxito sintetizó una amplia gama de sulfinamidas S-quirogénicas.
  • Logró una impresionante enantioselectividad en el proceso catalítico.
  • Demostró la estabilidad y adaptabilidad de las sulfinamidas sintetizadas para futuras transformaciones.

Conclusiones:

  • El método desarrollado catalizado por níquel proporciona una vía eficaz para las sulfinamidas enriquecidas enantioméricamente.
  • El estudio aclara los factores clave que rigen la enantioselectividad y los mecanismos de reacción.
  • Las sulfinamidas sintetizadas sirven como bloques de construcción valiosos para diversos compuestos que contienen azufre.