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Related Concept Videos

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
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Gold-catalyzed direct arylation.

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
Summary
This summary is machine-generated.

A new gold-catalyzed reaction enables direct biaryl synthesis from arenes and arylsilanes. This method offers a milder, more versatile alternative to traditional cross-coupling, simplifying the creation of valuable organic compounds.

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Biaryls are crucial structural units in pharmaceuticals, agrochemicals, and materials science.
  • Traditional synthesis relies heavily on cross-coupling reactions involving aryl halides and organometallic reagents.

Purpose of the Study:

  • To develop a novel, efficient, and site-selective method for biaryl bond formation.
  • To provide an alternative to existing cross-coupling methods, particularly for substrates with sensitive functional groups.

Main Methods:

  • Utilizing a gold catalyst (1-2 mol%) and a mild oxidant.
  • Employing arenes (Ar(1)-H) and arylsilanes (Ar(2)-SiMe(3)) as coupling partners.
  • Performing the reaction under mild, room-temperature conditions.

Main Results:

  • Achieved site-selective arylation of arenes by arylsilanes to form biaryls (Ar(1)-Ar(2)).
  • Minimized undesired homocoupling byproducts (Ar(1)-Ar(1)/Ar(2)-Ar(2)).
  • Demonstrated broad functional group tolerance, including groups incompatible with cross-coupling.

Conclusions:

  • The developed gold-catalyzed reaction provides a facile and efficient route to biaryls.
  • This methodology expands the synthetic toolkit for constructing complex organic molecules.
  • The process is exemplified by the synthesis of diflunisal, a nonsteroidal anti-inflammatory drug.