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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
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.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
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.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
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.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Published on: February 16, 2020

Arilación directa catalizada por el oro.

Liam T Ball1, Guy C Lloyd-Jones, Christopher A Russell

  • 1School of Chemistry, University of Bristol, Cantock's Close, Bristol, UK.

Science (New York, N.Y.)
|September 29, 2012
PubMed
Resumen
Este resumen es generado por máquina.

Una nueva reacción catalizada por oro permite la síntesis directa de biarilo a partir de arenos y arilsilanos. Este método ofrece una alternativa más suave y versátil al acoplamiento cruzado tradicional, simplificando la creación de valiosos compuestos orgánicos.

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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • La catálisis es la catálisis.
  • Metodología sintética de la metodología sintética.

Sus antecedentes:

  • Los biaryles son unidades estructurales cruciales en productos farmacéuticos, agroquímicos y ciencia de los materiales.
  • La síntesis tradicional se basa en gran medida en reacciones de acoplamiento cruzado que involucran haluros de arilo y reactivos organometálicos.

Objetivo del estudio:

  • Desarrollar un método novedoso, eficiente y selectivo del sitio para la formación de enlaces biarílicos.
  • Proporcionar una alternativa a los métodos de acoplamiento cruzado existentes, especialmente para sustratos con grupos funcionales sensibles.

Principales métodos:

  • Utilizando un catalizador de oro (1-2 mol%) y un oxidante suave.
  • Empleando arenos (Ar) y arilsilanos (Ar) como socios de acoplamiento.
  • Realizar la reacción bajo condiciones suaves, a temperatura ambiente.

Principales resultados:

  • Se obtiene la arilación selectiva del sitio de los arenos por arilsilanos para formar biarilos (Ar(1) -Ar(2)).
  • Se minimizan los subproductos no deseados del homoacoplamiento (Ar(1) -Ar(1) /Ar(2) -Ar(2)).
  • Amplia tolerancia demostrada al grupo funcional, incluyendo grupos incompatibles con el acoplamiento cruzado.

Conclusiones:

  • La reacción catalizada por oro desarrollada proporciona una ruta fácil y eficiente a los biarilos.
  • Esta metodología amplía el conjunto de herramientas sintéticas para la construcción de moléculas orgánicas complejas.
  • El proceso es ejemplificado por la síntesis de diflunisal, un fármaco antiinflamatorio no esteroide.